- Synthesis of malformin-A1, C, a glycan, and an aglycon analog: Potential scaffolds for targeted cancer therapy
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Improvement in therapeutic efficacy while reducing chemotherapeutic side effects remains a vital objective in synthetic design for cancer treatment. In keeping with the ethos of therapeutic development and inspired by the Warburg effect for augmenting biological activities of the malformin family of cyclic-peptide natural products, specifically anti-tumor activity, a β-glucoside of malformin C has been designed and synthesized utilizing precise glycosylation and solution phase peptide synthesis. We optimized several glycosylation procedures utilizing different donors and acceptors. The overarching goal of this study was to ensure a targeted delivery of a glyco-malformin C analog through the coupling of D-glucose moiety; selective transport via glucose transporters (GLUTs) into tumor cells, followed by hydrolysis in the tumor microenvironment releasing the active malformin C a glycon analog. Furthermore, total synthesis of malformin C was carried out with overall improved strategies avoiding unwanted side reactions thus increasing easier purification. We also report on an improved solid phase peptide synthesis protocol for malformin A1.
- Andreana, Peter R.,Hossain, Farzana,Nishat, Sharmeen
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- Controlled In-Cell Generation of Active Palladium(0) Species for Bioorthogonal Decaging
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Owing to their bioorthogonality, transition metals have become very popular in the development of biocompatible bond-cleavage reactions. However, many approaches require design and synthesis of complex ligands or formulation of nanoparticles which often perform poorly in living cells. This work reports on a method for the generation of an active palladium species that triggers bond-cleaving reactions inside living cells. We utilized the water-soluble Na2PdCl4 as a simple source of PdII which can be intracellularly reduced by sodium ascorbate to the active Pd0 species. Once generated, Pd0 triggers the cleavage of allyl ether and carbamate caging groups leading to the release of biologically active molecules. These findings do not only expand the toolbox of available bioorthogonal dissociative reactions but also provide an additional strategy for controlling the reactivity of Pd species involved in Pd-mediated bioorthogonal reactions.
- Bernardes, Gon?alo J. L.,Day, Jason,Domingos, Josiel B.,Jiménez-Moreno, Ester,Kon?, Juraj,Latocheski, Eloah,Pérez, Laura Rodríguez,Sabatino, Valerio
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supporting information
(2022/01/11)
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- Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride
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This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%-97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.
- Bannykh, Anton,Khomutnyk, Yaroslav,Kim, Sungjin,Nagorny, Pavel
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supporting information
p. 190 - 194
(2021/01/13)
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- An alternative approach for the synthesis of sulfoquinovosyldiacylglycerol
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Sulfoquinovosyldiacylglycerol (SQDG) is a glycolipid ubiquitously found in photosyn-thetically active organisms. It has attracted much attention in recent years due to its biological ac-tivities. Similarly, the increasing demand for vegan and functional foods has led to a growing interest in micronutrients such as sulfolipids and their physiological influence on human health. To study this influence, reference materials are needed for developing new analytical methods and providing enough material for model studies on the biological activity. However, the availability of these materials is limited by the difficulty to isolate and purify sulfolipids from natural sources and the unavailability of chemical standards on the market. Consequently, an alternative synthetic route for the comprehensive preparation of sulfolipids was established. Here, the synthesis of a sulfolipid with two identical saturated fatty acids is described exemplarily. The method opens possibilities for the preparation of a diverse range of interesting derivatives with different saturated and unsatu-rated fatty acids.
- Domey, Hendrik,Fischer, Judith,Rohn, Sascha,Sitz, Tobias
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- Self-Promoted Glycosylation for the Synthesis of β-N-Glycosyl Sulfonyl Amides
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N-Glycosyl N-sulfonyl amides have been synthesized by a self-promoted glycosylation, i. e. without any catalysts, promotors or additives. When the reactions were carried out at lower temperatures a mixture of N- and O-glycosides were observed, where the latter rearranged to give the β-N-glycosides at elevated temperatures. By this method sulfonylated asparagine derivatives can be selectively β-glycosylated in high yields by trichloroacetimidate glycosyl donors of different reactivity including protected glucosamine derivatives. The chemoselectivity in the glycosylations as well as the rearrangements from O-glycosides to β-N-glycosides gives information of the glycosylation mechanism. This method gives access to glycosyl sulfonyl amides under mild conditions.
- Ma?a, Patrycja,Pedersen, Christian Marcus
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supporting information
p. 5685 - 5689
(2021/08/30)
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- Preparation method of tetraacetyl glucose
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The invention belongs to the technical field of organic synthesis and relates to a preparation method of tetraacetylglucose. The invention provides a preparation method of tetraacetylglucose. According to the preparation method, bromo-tetraacetylglucose is adopted as a reaction substrate, a reaction is performed in a reaction system containing water, an organic solvent, a phase transfer catalyst and inorganic base under the action of an organic base catalyst to generate tetraacetylglucose; and the organic base catalyst is selected from any one component or a combination of components selected from triethylamine, diisopropylethylamine, pyridine, 2-methylpyridine, 2, 6-dimethylpyridine, 2, 4, 6-trimethylpyridine, 4-pyrrolidinyl pyridine, 4-morpholinyl pyridine and 4-dimethylamino pyridine.
- -
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Paragraph 0034-0050
(2021/04/07)
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- Rh2(II)-Catalyzed intermolecular N-Aryl aziridination of olefins using nonactivated N atom precursors
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The development of the first intermolecular Rh2(II)-catalyzed aziridination of olefins using anilines as nonactivated N atom precursors and an iodine(III) reagent as the stoichiometric oxidant is reported. This reaction requires the transfer of an N-aryl nitrene fragment from the iminoiodinane intermediate to a Rh2(II) carboxylate catalyst; in the absence of a catalyst only diaryldiazene formation was observed. This N-aryl aziridination is general and can be successfully realized by using as little as 1 equiv of the olefin. Di-, tri-, and tetrasubstituted cyclic or acylic olefins can be employed as substrates, and a range of aniline and heteroarylamine N atom precursors are tolerated. The Rh2(II)-catalyzed N atom transfer to the olefin is stereospecific as well as chemo- and diastereoselective to produce the N-aryl aziridine as the only amination product. Because the chemistry of nonactivated N-aryl aziridines is underexplored, the reactivity of N-aryl aziridines was explored toward a range of nucleophiles to stereoselectively access privileged 1,2-stereodiads unavailable from epoxides, and removal of the N-2,4-dinitrophenyl group was demonstrated to show that functionalized primary amines can be constructed.
- Deng, Tianning,Mazumdar, Wrickban,Yoshinaga, Yuki,Patel, Pooja B.,Malo, Dana,Malo, Tala,Wink, Donald J.,Driver, Tom G.
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supporting information
p. 19149 - 19159
(2021/11/23)
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- Total synthesis of three natural phenethyl glycosides
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Phenethyl glycosides having phenolic or methoxy functions at benzene rings are substances widely occurring in nature. This kind of compounds has been shown to have anti-oxidant, anti-inflammatory, and anticancer activities. However, some of them are not naturally abundant, thus the synthesis of such molecules is desirable. In this paper, natural phenethyl glycosides 3 and 4 were first totally synthesized from easily available materials with overall yields of 50.5% and 40.1%, respectively. And a new synthetic route to obtain natural phenethyl glycoside 2 in 46.2% yield was also described.
- Dong, Hong-Bo,Meng, Jian,Yao, Zhong-Quan,Luo, Hong-Bing,Zhang, Jing-Xia,Du, Wei-Hong,Tang, Ke-Hui,Cao, Sheng-Hua
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p. 284 - 293
(2020/03/03)
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- First total syntheses of two natural glycosides
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Isosyringinoside (1) and 3-(O-β-D-glucopyranosyl)-α-(O-β-D-glucopyranosyl)-4-hydroxy phenylethanol (2), the natural bioactive compounds contained unique structures, were first totally synthesized using easily available materials in short convenient routes with overall yields of 20.2% and 27.0%, respectively. An efficient total synthesis of 1 was developed in six steps, which contained two key steps of highly regioselective glycosylation without any selective protection steps. The seven-step synthesis of 2 involved two steps of regioselective glycosylations using BF3–O(C2H5)2 and TMSOTf as catalysts, respectively.
- Dong, Hongbo,Du, Weihong,Yao, Zhongquan,Wu, Min,Luo, Hongbing,He, Yujiao,Cao, Shenghua
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supporting information
(2020/12/02)
-
- Scalable Total Synthesis of Piceatannol-3′-O-β-d-glucopyranoside and the 4′-Methoxy Congener Thereof: An Early Stage Glycosylation Strategy
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Scalable syntheses of piceatannol-3'-O-β-D-glucopyranoside and the 4'-methoxy congener thereof were achieved. This route features an early implemented Fischer-like glycosylation reaction, a regioselective iodination of phenolic glycoside under strongly acidic conditions, a highly telescoped route to access the styrene derivative, and a key Mizoroki.Heck reaction to render the desired coupled products in high overall yield.
- Chen, Lei,Li, Jianfeng,Wang, Xiaoting,Zhang, Rong-Ping
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- 3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL
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The present invention relates to a 3'-ketoglycoside compound defined by formula (I) and its use for controlled release of alcohols, in particular alcohols showing an insect repellent effect. It relates also to a process for preparing the 3'-ketoglycoside compound of formula (I). It further relates to a composition comprising a 3'- ketoglycoside compound of formula (I). It relates also to the use of a 3'-ketoglycoside compound of formula (I) for the controlled release of alcohols. It related also to a method of use of such composition.
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Page/Page column 35
(2021/08/20)
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- A gulose moiety contributes to the belomycin (BLM) disaccharide selective targeting to lung cancer cells
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Eight mono- or disaccharide analogues derived from BLM disaccharide, along with the corresponding carbohydate-dye conjugates have been designed and synthesized in this study, aiming at exploring the effect of a gulose residue on the cellular binding/uptake of BLM disaccharide and it possible uptake mechanism. Our evidence is presented indicating that, for the cellular binding/uptake of BLM disaccharide, a gulose residue is an essential subunit but unrelated to its chemical nature. Interestingly, D-gulose-dye conjugate is able to selectively target A549 cancer cells, but L-gulose-dye conjugate fails. Further uptake mechanism studies demonstrate D-gulose-dye derivatives similar to BLM disaccharide-dye ones behave in a temperature- and ATP-dependent manner, and are partly directed by the GLUT1 receptor. Moreover, D-gulose modifying gemcitabine 53a exhibits more potent antitumor activity compared to derivatives 53b-c in which gemcitabine is decorated with other monosaccharides. Taken together, the monosacharide D-gulose conjugate offers a new strategy for solving cytotoxic drugs via the increased tumor targeting in the therapy of lung cancer.
- Cao, Yongjun,Chen, Wenming,Huang, Weiping,Li, Houkai,Liao, Guohao,Qi, Dongxia,Wang, Meizhu,Wang, Xiaoyang,Ye, Wenchong,Zhou, Cui,Zhou, Wen
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supporting information
(2021/10/07)
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- Mannose-modified azide exosome and application thereof
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The invention belongs to the field of biological medicine, and particularly relates to a mannose-modified azide exosome and an application thereof. The mannose-modified azide exosome is prepared through metabolic labeling and click chemistry reaction; the advantages of the surface-functionalized azide exosome targeting macrophages are determined through a flow cytometry on the cellular level, and in-vitro pharmacological experiments prove that the mannose-modified azide exosome has the advantage of treating infectious diseases after being loaded with drugs. According to the surface-functionalized azide exosome provided by the invention, the targeting property of the exosome as a drug carrier can be greatly improved, and the effect of the surface-functionalized azide exosome in treating refractory infectious related diseases is improved.
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Paragraph 0056; 0062; 0065
(2021/06/23)
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- Preparation and formulation optimization of methotrexate-loaded human serum albumin nanoparticles modified by mannose
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Background: Methotrexate (MTX) is the representative drug among the dis-ease-modifying anti-rheumatic drugs. However, the conventional treatment with MTX showed many limitations and side effects. Objective: To strengthen the targeting ability and circulation time of MTX in the treatment of rheumatoid arthritis, the present study focused on developing a novel drug delivery system of methotrexate-loaded human serum albumin nanoparticles (MTX-NPs) modified by mannose, which are referred to as MTX-M-NPs. Methods: Firstly, mannose-derived carboxylic acid was synthesized and further modified on the surface of MTX-NPs to prepare MTX-M-NPs. The formulation of nanoparticles was optimized by the method of central composite design (CCD), with the drug lipid ra-tio, oil-aqueous ratio, and cholesterol or lecithin weight as the independent variables. The average particle size and encapsulation efficiency were the response variables. The response of different formulations was calculated, and the response surface diagram, con-tour diagram, and mathematical equation were used to relate the dependent and independent variables to predict the optimal formula ratio. The uptake of MTX-M-NPs by neu-trophils was studied through confocal laser detection. Further, MTX-M-NPs were subject-ed to assessment of the pharmacokinetics profile after intravenous injection with Sprague-Dawley rats. Results: This targeting drug delivery system was successfully developed. Results from Nuclear Magnetic Resonance and Fourier Transform Infrared Spectroscopy analysis can verify the successful preparation of this drug delivery system. Based on the optimized for-mula, MTX-M-NPs were prepared with a particle size of 188.17 ± 1.71 nm and an encapsulation rate of 95.55 ± 0.33%. MTX-M-NPs displayed significantly higher cellular uptake than MTX-NPs. The pharmacokinetic results showed that MTX-M-NPs could pro-long the in vivo circulation time of MTX. Conclusion: This targeting drug delivery system laid a promising foundation for the treatment of RA.
- Chen, Zhenyu,Lin, Yan,Liu, Zhongbing,Luo, Zhongling,Lyu, Jiayao,Wang, Jianxin,Wei, Jun,Zhong, Zhirong
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p. 5016 - 5029
(2021/08/17)
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- Fluorinated rhamnosides inhibit cellular fucosylation
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The sugar fucose is expressed on mammalian cell membranes as part of glycoconjugates and mediates essential physiological processes. The aberrant expression of fucosylated glycans has been linked to pathologies such as cancer, inflammation, infection, and genetic disorders. Tools to modulate fucose expression on living cells are needed to elucidate the biological role of fucose sugars and the development of potential therapeutics. Herein, we report a class of fucosylation inhibitors directly targeting de novo GDP-fucose biosynthesis via competitive GMDS inhibition. We demonstrate that cell permeable fluorinated rhamnose 1-phosphate derivatives (Fucotrim I & II) are metabolic prodrugs that are metabolized to their respective GDP-mannose derivatives and efficiently inhibit cellular fucosylation.
- Boltje, Thomas J.,Eerden, Nienke,Lefeber, Dirk J.,Merx, Jona,Noga, Marek J.,Pijnenborg, Johan F. A.,Rossing, Emiel,Titulaer, Willem H. C.,Veizaj, Raisa,White, Paul B.
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- Eradicating intracellular MRSA via targeted delivery of lysostaphin and vancomycin with mannose-modified exosomes
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Intracellular methicillin-resistant Staphylococcus aureus (MRSA) is extremely difficult to remove by common antibiotics, leading to infection recurrence and resistance. Herein we report a novel exosome-based antibiotic delivery platform for eradicating intracellular MRSA, where mannosylated exosome (MExos) is employed as the drug carrier and preferentially taken up by macrophages, delivering lysostaphin (MExoL) and vancomycin (MExoV) to intracellular pathogens. Combination of MExoL and MExoV eradicated intracellular quiescent MRSA. Moreover, MExos rapidly accumulated in mouse liver and spleen, the target organs of intracellular MRSA, after intravenous (IV) administration. Thus, the MExos antibiotic delivery platform is a promising strategy for combating intracellular infection.
- Yang, Xiaohong,Xie, Beibei,Peng, Haibo,Shi, Gongming,Sreenivas, Banne,Guo, Jian,Wang, Chenhui,He, Yun
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p. 454 - 467
(2020/12/25)
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- Synthetic method of empagliflozin
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The invention belongs to the technical field of raw material medicine preparation, and relates to a synthetic method of an SGLT-2 inhibitor empagliflozin, which comprises the following steps: 1) taking glucose as an initial raw material, and preparing an active intermediate 3 through full acylation, selective hydrolysis and esterification; 2) reacting the intermediate 3 with chlorobenzene under the catalysis of boron trifluoride/diethyl ether to generate an intermediate 4, and reacting the intermediate 4 with paraformaldehyde and phenoxy tetrahydrofuran to generate an intermediate 5; and 3) removing the protecting group under the action of alkali to obtain the final product empagliflozin. The method is simple to operate, low-temperature reaction in the prior art is avoided, and the purity of the obtained product is higher.
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Paragraph 0019-0021
(2021/07/24)
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- GLYCOSIDE COMPOUND AND PREPARATION METHOD THEREFOR, COMPOSITION, APPLICATION, AND INTERMEDIATE
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The present invention discloses a glycoside compound represented by Formula III, and a preparation method, a composition, use and an intermediate thereof. The glycoside compound provided in the present invention has simple preparation method, can significantly increase the expression of VEGF-A mRNA, and is effective in promoting the angiogenesis. This provides a reliable guarantee for the development of drugs with pro-angiogenic activity for treating cerebral infarction cerebral stroke, myocardial infarction, and ischemic microcirculatory disturbance of lower limbs.
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Paragraph 0402; 0407
(2021/04/23)
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- NOVEL BENZIMIDAZOLE DERIVATIVES, PREPARATION METHOD THEREOF AND USE THEREOF AS ANTI-CANCER AGENT COMPRISING THE SAME
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According to the present invention, there are provided a benzimidazole carbamate-sugar compound conjugate compound represented by the following Chemical Formula 1, a preparation method thereof, and a use thereof as an anti-cancer agent: Wherein, R1, R2, R3 and X are as defined in the specification and claims.
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Paragraph 0186-0190
(2021/10/02)
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- Nanoparticles to Study Lectins in Caenorhabditis elegans: Multivalent Galactose β1-4 Fucose-Functionalized Dendrimers Provide Protection from Oxidative Stress
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Galectins are galactoside-binding lectins that are functional dimers or higher-order oligomers. Multivalent binding has been shown to augment the relatively low affinity of the galectins for their galactoside-binding partners, enabling the galectins to pl
- Vankoten, Harrison W.,Moore, Rebecca S.,Cloninger, Mary J.
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p. 4720 - 4729
(2021/11/17)
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- Synthesis of photolabile group protected anomeric acetals and its application in carbohydrate synthesis with the assistance of continuous flow photo-reactor
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Selective deprotection of photolabile anomeric 2-nitrobenzyl acetals was achieved using continuous flow photo-reactor (UV radiation at 355 nm) in methanol-water. Various protecting groups such as acetyl, benzyl, benzoyl, benzylidine, TBS, etc. were found to be highly stable during the photolysis.
- Tiwari, Varsha,Badavath, Vishnu Nayak,Singh, Adesh Kumar,Kandasamy, Jeyakumar
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p. 227 - 236
(2020/03/18)
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- Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2-Aryl-1,3-dithiane 1-Oxide?
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A new dehydrative glycosylation reaction has been established by capitalizing on the comproportionation reaction of 2-aryl-1,3-dithiane 1-oxides promoted by triflic anhydride (Tf2O). By wedding the high potency of thiophilic promoter system with the step efficiency of dehydrative glycosylation, this reagent underwent facile intermolecular oxothio acetalization with C1-hemiacetal donor to install a temporary leaving group, rendering a transient electrophilic center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3-diol protection. Most importantly, this method further provided a fresh perspective for the application of sulfur chemistry to carbohydrate chemistry.
- Cai, Lei,Zeng, Jing,Li, Ting,Xiao, Ying,Ma, Xiang,Xiao, Xiong,Zhang, Qin,Meng, Lingkui,Wan, Qian
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supporting information
p. 43 - 49
(2019/11/28)
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- Chemical glucosylation of pyridoxine
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The chemical synthesis of pyridoxine-5′-β-D-glucoside (5′-β-PNG) was investigated using various glucoside donors and promoters. Hereby, the combination of α4,3-O-isopropylidene pyridoxine, glucose vested with different leaving and protecting groups and the application of stoichiometric amounts of different promoters was examined with regards to the preparation of the twofold protected PNG. Best results were obtained with 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl fluoride and boron trifluoride etherate (2.0 eq.) as promoter at 0 °C (59%). The deprotection was accomplished stepwise with potassium/sodium hydroxide in acetonitrile/water followed by acid hydrolysis with formic acid resulting in the chemical synthesis of 5′-β-PNG.
- Bachmann, Thomas,Rychlik, Michael
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supporting information
(2020/02/13)
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- Short gram-scale synthesis of sulfavant A
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Recently, we reported the promising activity of a novel class of sulfoquinovosyl-diacylglycerols named Sulfavants as molecular vaccine adjuvants. Herein, we describe a modified and improved chemical synthesis of the lead product Sulfavant A (1), with the aim to produce from milligrams to 10 g of the pure compound that is necessary for the preclinical development. Starting from the versatile synthesis based on the trichloroacetimidate methodology, up-scaled preparation of Sulfavant A (1) was achieved in 11 steps by elimination and modification of those reactions that negatively affected the overall yield by the previous procedure. The novel strategy gave 17% overall yield of the target compound 1 and also paved the way for the gram-scale preparation of a wide range of other charged and neutral glycoglycerolipids.
- Ziaco, Marcello,Fioretto, Laura,Nuzzo, Genoveffa,Fontana, Angelo,Manzo, Emiliano
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p. 2728 - 2733
(2020/11/18)
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- Synthesis and cytotoxic property of annonaceous acetogenin glycoconjugates
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Background: Annonaceous acetogenins (ACGs) are secondary metabolites produced by the Annonaceae family and display potent anticancer activity against various cancer cell lines. Squamocin and bullatacin are two examples of ACGs that show promising antitumor activity; however, preclinical data are not sufficient partly due to their being highly lipophilic and poorly soluble in water. These compounds also display high toxicity to normal cells. Due to these disadvantageous properties, the therapeutic potential of squamocin and bullatacin as antitumor agents has not been fully evaluated. Methods: In order to enhance their water solubility and potentially improve their cancer targeting, squamocin and bullatacin were conjugated to a glucose or galactose to yield glycosylated derivatives by direct glycosylation or the Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reaction (the click reaction). The synthesized compounds were evaluated for their anticancer property against HeLa, A549 and HepG2 cancer cell lines using MTT assay. Results: Nine glycosyl derivatives were synthesized and structurally characterized. Most of them show comparable in vitro cytotoxicity against HeLa, A549 and HepG2 cancer cell lines as their parent compounds squamocin and bullatacin. It appears that the type of sugar residue (glucose or galactose), the position at which the sugar residue is attached, and whether or not a linking spacer is present do not affect the potency of these derivatives much. The solubility of galactosylated squamocin 13 in phosphate buffer saline (PBS, pH = 7) is greatly improved (1.37 mg/mL) in comparison to squamocin (not detected in PBS). Conclusion: The conjugation of a glucose or galactose to squamocin and bullatacin yields glycosyl derivatives with similar level of anticancer activity in tested cell lines. Further studies are needed to demonstrate whether or not these compounds show reduced toxicity to normal cells and their therapeutic potential as antitumor agents.
- Shi, Jing-Fang,Wu, Ping,Cheng, Xiao-Li,Wei, Xiao-Yi,Jiang, Zi-Hua
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p. 4993 - 5004
(2020/11/23)
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- Studies on the stereoselective synthesis and immunosuppressive activity of dihydroartemisinin-O-glycoside derivatives
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Eight new dihydroartemisinin-O-glycosides were synthesized with their relative configurations were determined based on NMR spectrum. In vitro immunosuppressive assay showed that 10α-dihydroartemisinin-β-O-D-mannoside (19a) demonstrate 88percent inhibition towards T cells proliferation and 98percent reduction in IFN-γ levels in cell media. These results suggest that dihydroartemisinin-O-glycoside as a potential lead for further in vivo evaluation.
- Bian, Hongzhu,Dong, Xun,Shen, Zhengwu,Xu, Wei,Yu, Jingfeng,Yu, Yu,Zhang, Jinghua,Zou, Xiaosu
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supporting information
(2020/07/21)
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- Pivaloyl-protected glucosyl iodide as a glucosyl donor for the preparation of β-C-glucosides
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A method for the selective synthesis of β-C-glucosides using α-D-tetra-O-pivaloylglucosyl iodide as a glucosyl donor is reported. Its diastereoselectivity differs from that of the respective acetyl-protected glucosyl bromide, as it reported in the literature under similar reaction conditions. The concentration of the catalyst, the solvent and the type of additive used are crucial factors that determine the reaction selectivity. This method has been applied in a short synthesis of dapagliflozin. The stability of α-D-tetra-O-pivaloylglucosyl iodide in CDCl3 and THF at reflux was also studied. All side products in the coupling and decomposition reactions were isolated and characterized, and possible pathways for their formation are proposed.
- Triantakonstanti, Virginia V.,Toskas, Alexandros,Iordanidis, Nicolaos S.,Andreou, Thanos,Koftis, Theoharis V.,Gallos, John K.
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supporting information
(2020/07/13)
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- Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation
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Several glycoconjugates of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with a 1,2,3-triazolyl moiety were synthesized, and their cytotoxicity was evaluated against some human cancer and normal cell lines. Most of the synthesized compounds demonstrated weak inhibitory activities against the M-HeLa and MCF-7 human cancer cell lines. Three lead compounds, 54, 56 and 57, exhibited high selective cytotoxic activity against M-HeLa cells (IC50 = 1.7-1.9 μM) that corresponded to the activity of the anticancer drug doxorubicin (IC50 = 3.0 μM). Moreover, the lead compounds were not cytotoxic with respect to a Chang liver human normal cell line (IC50 > 100 μM), whereas doxorubicin was cytotoxic to this cell line (IC50 = 3.0 μM). It was found that cytotoxic activity of the lead compounds is due to induction of apoptosis proceeding along the mitochondrial pathway. The present findings suggest that 1,2,3-triazolyl-ring-containing glycoconjugates of isosteviol are a promising scaffold for the design of novel anticancer agents.
- Andreeva, Olga V.,Garifullin, Bulat F.,Sharipova, Radmila R.,Strobykina, Irina Yu.,Sapunova, Anastasiya S.,Voloshina, Alexandra D.,Belenok, Mayya G.,Dobrynin, Alexey B.,Khabibulina, Leysan R.,Kataev, Vladimir E.
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p. 2367 - 2380
(2020/08/28)
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- Carbonyl compound containing amino acid connecting chain or pharmaceutically acceptable salt thereof, and preparation method and application of carbonyl compound
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The invention provides a carbonyl compound containing an amino acid connecting chain or a pharmaceutically acceptable salt thereof as well as a preparation method and application of the carbonyl compound, and belongs to the technical field of anti-AIDS medicines. The carbonyl compound containing the amino acid connecting chain or the pharmaceutically acceptable salt thereof provided by the invention has a structure shown as formula I in the specification. The carbonyl compound containing the amino acid connecting chain or the pharmaceutically acceptable salt thereof provided by the inventionhas obvious activity of inhibiting HIV protease; the obvious inhibition activity is realized on the DRV drug-resistant strain; toxicity research shows that the compound is low in toxicity and has gooddruggability; the inhibitory activity on HIV-1 protease is 286-1052 times of the inhibitory activity of a positive control drug DRV on HIV-1 protease; the inhibitory activity on a DRV drug-resistantstrain and the inhibitory activity on a wild HIV-1 drug-resistant strain are only reduced by 1.10-3.23 times, and the compound has a good application prospect as an anti-AIDS drug.
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Paragraph 0215; 0227-0229
(2020/06/16)
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- Preparation, supramolecular aggregation and immunological activity of the bona fide vaccine adjuvant sulfavant S
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In aqueous conditions, amphiphilic bioactive molecules are able to form self-assembled colloidal structures modifying their biological activity. This behavior is generally neglected in preclinical studies, despite its impact on pharmacological development. In this regard, a significative example is represented by a new class of amphiphilic marine-inspired vaccine adjuvants, collectively named Sulfavants, based on the β-sulfoquinovosyl-diacylglyceride skeleton. The family includes the lead product Sulfavant A (1) and two epimers, Sulfavant R (2) and Sulfavant S (3), differing only for the stereochemistry at C-2 of glycerol. The three compounds showed a significant difference in immunological potency, presumably correlated with change of the aggregates in water. Here, a new synthesis of diastereopure 3 was achieved, and the study of the immunomodulatory behavior of mixtures of 2/3 proved that the bizarre in vitro response to 1–3 effectively depends on the supramolecular aggregation states, likely affecting the bioavailability of agonists that can effectively interact with the cellular targets. The evidence obtained with the mixture of pure Sulfavant R (2) and Sulfavant S (3) proves, for the first time, that supramolecular organization of a mixture of active epimers in aqueous solution can bias evaluation of their biological and pharmacological potential.
- Manzo, Emiliano,Fioretto, Laura,Gallo, Carmela,Ziaco, Marcello,Nuzzo, Genoveffa,D’Ippolito, Giuliana,Borzacchiello, Assunta,Fabozzi, Antonio,de Palma, Raffaele,Fontana, Angelo
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- Tea leaf perfumery precursor glucoside and synthesizing method thereof
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The invention relates to a tea leaf perfumery precursor glucoside and a synthesizing method thereof. The synthesizing method comprises the following steps of synthesizing ten glucosides including aromatic alcohol ( alkanol )-beta -D-glucosides and aromatic alcohol (alkanol )-beta -D-primrose indicans. The synthesizing method disclosed by the invention is a glucoside synthesizing method which is good in selectivity, high in production rate and low in cost.
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Paragraph 0044-0046; 0050-0051
(2020/07/02)
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- Chemoenzymatic synthesis of arabinomannan (AM) glycoconjugates as potential vaccines for tuberculosis
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Mycobacteria infection resulting in tuberculosis (TB) is one of the top ten leading causes of death worldwide in 2018, and lipoarabinomannan (LAM) has been confirmed to be the most important antigenic polysaccharide on the TB cell surface. In this study, a convenient synthetic method has been developed for synthesizing three branched oligosaccharides derived from LAM, in which a core building block was prepared by enzymatic hydrolysis in flow chemistry with excellent yield. After several steps of glycosylations, the obtained oligosaccharides were conjugated with recombinant human serum albumin (rHSA) and the ex-vivo ELISA tests were performed using serum obtained from several TB-infected patients, in order to evaluate the affinity of the glycoconjugate products for the human LAM-antibodies. The evaluation results are positive, especially compound 21 that exhibited excellent activity which could be considered as a lead compound for the future development of a new glycoconjugated vaccine against TB.
- Li, Zhihao,Bavaro, Teodora,Tengattini, Sara,Bernardini, Roberta,Mattei, Maurizio,Annunziata, Francesca,Cole, Richard B.,Zheng, Changping,Sollogoub, Matthieu,Tamborini, Lucia,Terreni, Marco,Zhang, Yongmin
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supporting information
(2020/07/27)
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- Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34
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A general and efficient strategy for synthesis of tri-, hexa- and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α-linked galactosamine and the two embedded α-fucose units, which are either branched at positions-3 and -4 or further linked at their 2-position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.
- Ahadi, Somayeh,Awan, Shahid I.,Werz, Daniel B.
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supporting information
(2020/05/04)
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- Oligosaccharide-camptothecin conjugates as potential antineoplastic drugs: Design, synthesis and biological evaluation
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Thirty novel 20 (S)–O-linked camptothecin (CPT) glycoconjugates were synthesized. They showed more potent in vitro cytotoxicities over irinotecan, but very weak direct topoisomerase I (Topo I) inhibition was observed at 100.0 μM. Oligosaccharide types, length of a PEG linker and acetyl groups exerted obvious effects on cytotoxicity, selectivity, water solubility and stability of the newly synthesized CPT glycoconjugates. Construct 40, with a bleomycin (BLM) disaccharide linked to diethylene glycol in the introduced ester moiety, demonstrated a superior antitumor activity and a distinct selectivity compared to CPT. No toxicity was detectable in animal acute toxicity intravenously (160 mg/kg). Collectively, attachment of oligosaccharides with tumor targeting to 20 (S)–OH of CPT could offer a solution to the daunting problems posed by current Topo I poisons.
- Li, Maolin,Ye, Wenchong,Fu, Kaishuo,zhou, Cui,Shi, Yonghui,Huang, Weiping,Chen, Wenming,Hu, Jiliang,Jiang, Zhilin,Zhou, Wen
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- Synthesis of (-)-epigallocatechin-3-gallate derivative containing a triazole ring and combined with cisplatin/paclitaxel inhibits NSCLC cancer cells by decreasing phosphorylation of the EGFR
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Non-small-cell lung cancer is one of the principal causes of cancer-related death around the world. Chemotherapy is commonly used to treat wild type of epidermal growth factor receptor non-small-cell lung cancer. (-)-Epigallocatechin-3-gallate is the most abundant and active catechin. However, (-)-epigallocatechin-3-gallate has limited clinical application due to its poor stability and absorption. Herein, we report that a glycosylated azide undergoes a click reaction with the terminal alkyne of (-)-epigallocatechin-3-gallate to yield a triazole-linked glucose-(-)-epigallocatechin-3-gallate derivative and have evaluated its in vitro anticancer activity against human non-small-cell lung cancer cells using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. The product inhibits human non-small-cell lung cancer cell lines with wild type of epidermal growth factor receptor and in combination with cisplatin/paclitaxel results in more pronounced proliferation inhibition than when used alone. Stability investigations indicates that the conjugated glucose residue can improve the stability of the (-)-epigallocatechin-3-gallate scaffold. Our studies suggest that the combination of the glucose-(-)-epigallocatechin-3-gallate derivative and chemotherapeutic drugs may provide a novel strategy for the treatment of non-small-cell lung cancer.
- Zi, Cheng-Ting,Sun, Pei-Yuan,Zhang, Ning,Tang, Han,Yang, Hao-Nang,Wang, Qi,Wang, Yu-Na,Wang, Jing,Wang, Xuan-Jun,Sheng, Jun
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p. 586 - 591
(2020/04/22)
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- Low-budget 3D-printed equipment for continuous flow reactions
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This article describes the development and manufacturing of lab equipment, which is needed for the use in flow chemistry. We developed a rack of four syringe pumps controlled by one Arduino computer, which can be manufactured with a commonly available 3D printer and readily available parts. Also, we printed various flow reactor cells, which are fully customizable for each individual reaction. With this equipment we performed some multistep glycosylation reactions, where multiple 3D-printed flow reactors were used in series.
- Neumaier, Jochen M.,Madani, Amiera,Klein, Thomas,Ziegler, Thomas
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supporting information
p. 558 - 566
(2019/03/13)
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- Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature
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Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including α-mannose, and it was demonstrated here how the interaction between carbohydrates and boronic acids can be combined with copper catalysis to achieve selective anomeric O-arylation.
- Verdelet, Tristan,Benmahdjoub, Sara,Benmerad, Belkacem,Alami, Mouad,Messaoudi, Samir
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p. 9226 - 9238
(2019/08/12)
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- Facile synthesis of sugar lactols via bromine-mediated oxidation of thioglycosides
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Synthesis of a variety of sugar lactols (hemiacetals) has been accomplished in moderate to excellent yields by using bromine-mediated oxidation of thioglycosides. It was found that acetonitrile is the optimal solvent for this oxidation reaction. This approach involving bromine as oxidant is superior to that using N-bromosuccinimide (NBS) which produces byproduct succinimide often difficult to separate from the lactol products.
- Meng, Shuai,Bhetuwal, Bishwa Raj,Acharya, Padam P.,Zhu, Jianglong
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p. 109 - 126
(2019/03/26)
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- Towards a Synthetic Strategy for the Ten Canonical Carrageenan Oligosaccharides – Synthesis of a Protected γ-Carrageenan Tetrasaccharide
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Herein, we report a synthetic strategy aiming at synthesizing the ten canonical carrageenan oligosaccharides from one single precursor. The key β-(1→4)-linked disaccharide was synthesized from commercially available galactose pentaacetate. The notoriously difficult formation of β-(1→4)-d-galactan linkages was successfully optimized on the differentially substituted monosaccharides to afford the desired disaccharide in 55 % yield. Following a convergent strategy, two disaccharides were then glycosylated to form the fully protected α-(1→4)-linked tetrasaccharide backbone of the carrageenans. The careful selection of protecting groups provides the opportunity to access all ten carrageenan substructures identified in polysaccharides isolated from red algae. Here, we demonstrate how one such target oligosaccharide can be obtained in a protected form.
- Kinnaert, Christine,Clausen, Mads H.
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supporting information
p. 3236 - 3243
(2019/06/08)
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- Design, synthesis and bioactivity of core 1 O-glycan and its derivative on human gut microbiota
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Background: Disaccharide core 1 (Galβ1-3GalNAc) is a common O-glycan structure in nature. Biochemical studies have confirmed that the formation of the core 1 structure is an important initial step in O-glycan biosynthesis and it is of great importance for human body. Objective: Our study will provide meaningful and useful sights for O-glycan synthesis and their bioassay. And all the synthetic glycosides would be used as intermediate building blocks in the scheme developed for oligosaccharide construction. Methods: In this article, we firstly used chemical procedures to prepare core 1 and its derivative, and a novel disaccharide was efficiently synthesized. The structures of the synthesized compounds were elucidated and confirmed by 1H NMR, 13C NMR and MS. Then we employed three human gut symbionts belonging to Bacteroidetes, a predominantphyla in the distal gut, as models to study the bioactivity of core 1 and its derivative on human gut microbiota. Results: According to our results, both core 1 and derivative could support the growth of B. fragilis, especially the core 1 derivative, while failed to support the growth of B. thetaiotaomicron and B. ovatus. Conclusion: This suggested that the B. fragilis might have the specificity glycohydrolase to cut the glycosidic bond for acquiring monosaccharide.
- Qu, Huanhuan,Li, Baixue,Yang, Jingyi,Liang, Huaiwen,Li, Meixia,Ding, Kan
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p. 1348 - 1353
(2019/11/22)
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- Synthesis of 13C-labelled sulfated N-acetyl-d-lactosamines to aid in the diagnosis of mucopolysaccharidosis diseases
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Morquio A syndrome is an autosomal mucopolysaccharide storage disorder that leads to accumulation of keratan sulfate. Diagnosis of this disease can be aided by measuring the levels of keratan sulfate in the urine. This requires the liquid chromatography tandem mass spectrometry (LCMS/MS) measurement of sulfated N-acetyl-d-lactosamines in the urine after cleavage of the keratan sulfate with keratanase II. Quantification requires isotopically-labelled internal standards. The synthesis of these 13C6-labelled standards from 13C6-galactose and N-acetylglucosamine is described. The required protected disaccharide is prepared utilising a regioselective, high yielding β-galactosylation of a partially protected glucosamine acceptor and an inverse addition protocol. Subsequent synthesis of the 13C6-labelled mono and disulfated N-acetyllactosamines was achieved in five and eight steps, respectively, from this intermediate to provide internal standards for the LCMS/MS quantification of keratan sulfate in urine.
- Cameron, Scott A.,Zubkova, Olga V.,Toms, Steven,Furneaux, Richard H.,Rendle, Phillip M.
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- Synthesis, chemical characterization and antimicrobial activity of new acylhydrazones derived from carbohydrates
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A new series of glycosylated acylhydrazones was synthesized and all the chemical structures were confirmed by High Resolution Mass Spectrometry (HRMS), 1H and 13C Nuclear Magnetic Resonance (1H-NMR; 13C-NMR) and Fourier Transform Infrared (FTIR) spectroscopy methods. The mass accuracy between the calculated and found values observed in HRMS analyses were near or lower than 5 ppm, which are acceptable for proposing a molecular formula using this technique. All of the synthesized compounds were screened for their antibacterial, antifungal and antiviral activities. Five compounds (12, 13, 14, 16 and 19) exerted a modest antifungal activity against the strains evaluated. Derivative 14 showed fungicidal activity against Candida glabrata at 173.8 μM and saccharide unit contributed to the increase of the antifungal potential against this strain. New chemical manipulation of derivative 14 can make it possible to obtain new potentially antimicrobial agents.
- Guilherme, Fernanda Dias,Simonetti, Julia évelin,Folquitto, Lais Regina Santos,Reis, Adriana Cotta Cardoso,Oliver, Josidel Concei??o,Dias, Amanda Latércia Tranches,Dias, Danielle Ferreira,Carvalho, Diogo Teixeira,Brand?o, Geraldo Célio,Souza, Thiago Belarmino de
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p. 349 - 356
(2019/03/04)
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- Streamlining routine organic chemistry reactions by the employment of high shear mixers
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Some organic reactions involve long reaction times and high energy consumption. Herein, an improved method to accelerate the reactions by the employment of a high shear mixer is described. The produced emulsion minimizes the mass transfer resistance and reaction times, improves yields, and saves energy, in agreement with the Green Chemistry principles.
- Zeferino-Díaz, Reyna,Hilario-Martínez, J. Ciciolil,Sánchez-Cantú, Manuel,Fernández-Herrera, María A.,Sandoval-Ramirez, Jesus
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supporting information
p. 1417 - 1420
(2019/03/26)
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- Glucoside derivatives of podophyllotoxin: Synthesis, physicochemical properties, and cytotoxicity
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Background: Widespread concern of the side effects and the broad-spectrum anticancer property of podophyllotoxin as an antitumor agent highlight the need for the development of new podophyllotoxin derivatives. Although some per-butyrylated glucosides of podophyllotoxin and 4β-triazolyl-podophyllotoxin glycosides show good anticancer activity, the per-acetylated/free of podophyllotoxin glucosides and their per-acetylated are not well studied. Methods: A few glucoside derivatives of PPT were synthesized and evaluated for their in vitro cytotoxic activities against five human cancer cell lines, HL-60 (leukemia), SMMC-7721 (hepatoma), A-549 (lung cancer), MCF-7 (breast cancer), and SW480 (colon cancer), as well as the normal human pulmonary epithelial cell line (BEAS-2B). In addition, we investigated the structure–activity relationship and the physicochemical property–anticancer activity relationship of these compounds. Results: Compound 6b shows the highest cytotoxic potency against all five cancer cell lines tested, with IC50 values ranging from 3.27±0.21 to 11.37±0.52 μM. We have also found that 6b displays higher selectivity than the etoposide except in the case of HL-60 cell line. The active compounds possess similar physicochemical properties: MSA > 900, %PSA 2, MW > 700 Da, and RB > 10. Conclusion: We synthesized several glucoside derivatives of PPT and tested their cytotoxicity. Among them, compound 6b showed the highest cytotoxicity. Further studies including selectivity of active compounds have shown that the selectivity indexes of 6b are much greater than the etoposide except in the case of HL-60 cell line. The active compounds possessed similar physicochemical properties. This study indicates that active glucoside analogs of podophyllotoxin have potential as lead compounds for developing novel anticancer agents.
- Zi, Cheng-Ting,Yang, Liu,Kong, Qing-Hua,Li, Hong-Mei,Yang, Xing-Zhi,Ding, Zhong-Tao,Jiang, Zi-Hua,Hu, Jiang-Miao,Zhou, Jun
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p. 3683 - 3692
(2019/11/05)
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- Synthesis and O-Glycosidic Linkage Conformational Analysis of 13C-Labeled Oligosaccharide Fragments of an Antifreeze Glycolipid
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NMR studies of two 13C-labeled disaccharides and a tetrasaccharide were undertaken that comprise the backbone of a novel thermal hysteresis glycolipid containing a linear glycan sequence of alternating [βXylp-(1→4)-βManp-(1→4)]n dimers. Experimental trans-glycoside NMR J-couplings, parameterized equations obtained from density functional theory (DFT) calculations, and an in-house circular statistics package (MA'AT) were used to derive conformational models of linkage torsion angles φ and ψ in solution, which were compared to those obtained from molecular dynamics simulations. Modeling using different probability distribution functions showed that MA'AT models of φ in βMan(1→4)βXyl and βXyl(1→4)βMan linkages are very similar in the disaccharide building blocks, whereas MA'AT models of ψ differ. This pattern is conserved in the tetrasaccharide, showing that linkage context does not influence linkage geometry in this linear system. Good agreement was observed between the MA'AT and MD models of ψ with respect to mean values and circular standard deviations. Significant differences were observed for φ, indicating that revision of the force-field employed by GLYCAM is probably needed. Incorporation of the experimental models of φ and ψ into the backbone of an octasaccharide fragment leads to a helical amphipathic topography that may affect the thermal hysteresis properties of the glycolipid.
- Zhang, Wenhui,Meredith, Reagan,Yoon, Mi-Kyung,Wang, Xiaocong,Woods, Robert J.,Carmichael, Ian,Serianni, Anthony S.
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p. 1706 - 1724
(2019/02/14)
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- Monosaccharide Analogues of Anticancer Peptide R-Lycosin-I: Role of Monosaccharide Conjugation in Complexation and the Potential of Lung Cancer Targeting and Therapy
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Glycoconjugation is a promising modification strategy for the optimization of peptide drugs. In this study, five different monosaccharide derivatives (7a-e) were covalently linked to the N-terminal of R-lycosin-I, which yielded five glycopeptides (8a-e). They demonstrated increased or reduced cytotoxicity depending on monosaccharide types, which might be explained by the changes of physicochemical properties. Among all synthesized glycopeptides, only 8a exhibited increased cytotoxicity (IC50 = 9.6 ± 0.3 μM) and selectivity (IC50 = 37.4 ± 5.9 μM). The glucose transporter 1 (GLUT1) with high expression in cancer cells was approved to be involved in the cytotoxicity and selectivity enhancement of 8a. Furthermore, 8a but not R-lycosin-I inhibited tumor growth in the nude mice xenograft model without generating side effects intraperitoneally. Taken together, this study reveals the different monosaccharide roles in peptide modification and also provides an optimized anticancer peptide with high activity and selectivity, that is, 8a might be a promising lead for developing anticancer drugs.
- Zhang, Peng,Ma, Jing,Zhang, Qianqian,Jian, Shandong,Sun, Xiaoliang,Liu, Bobo,Nie, Liqin,Liu, Meiyan,Liang, Songping,Zeng, Youlin,Liu, Zhonghua
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p. 7857 - 7873
(2019/10/11)
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- A Dinuclear Dysprosium Complex as an Air-Stable and Recyclable Catalyst: Applications in the Deacetylation of Carbohydrate, Aliphatic, and Aromatic Molecules
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Two dinuclear DyIII complexes, [Dy2(hmb)2(OTf)2(H2O)4]?HOTf?2 THF (A?HOTf?2 THF) and [Dy2(hmi)3(H2O)2]?2 HOTf (B?2 HOTf), have been synthesized by the reaction of Dy(OTf)3 and the Schiff-base ligands H2hmb (N′-(2-hydroxy-3-methoxybenzylidene)benzohydrazide) or H2hmi ((2-hydroxy-3-methoxyphenyl)methylene isonicotinohydrazine). Disarmed glycosyl trichloroacetimidates can be activated by complex A in the synthesis of 1,2-trans-glycosides with primary and secondary acceptors. This method offers an efficient route to selectively deacetylated monosaccharides and disaccharides in high yields and a green catalyst that can be easily recycled and reused.
- Chiu, Ting-Yu,Chin, Wei,Guo, Jiun-Rung,Liang, Chien-Fu,Lin, Po-Heng
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supporting information
p. 627 - 633
(2019/02/09)
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- Chemical synthesis method of Bacillus pyocyaneus 011 serotype O antigen oligosaccharide
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The invention discloses a chemical synthesis method of Bacillus pyocyaneus 011 serotype O antigen oligosaccharide, and belongs to the field of chemistry. The method comprises the steps that a D-glucose block, an L-fucosamine block and a D-fucosimide block are utilized to construct O antigen trisaccharide, wherein the D-glucose block or the L-fucosamine block is connected with the D-fucosimide block through a 1,2-alpha-cis-glycosidic bond, the D-glucose block is connected with the L-fucososamine block through a 1,2-alpha-trans-glycosidic bond, and the 1,2-alpha-cis-glycosidic bond is constructed in a mixed solvent; the mixed solvent comprises two or more of dichloromethane, diethyl ether and thiophene. The method has the advantages that D-mannose is utilized as a raw material to obtain D-fucose simply, conveniently and efficiently; the uniform construction of the cis-glycosidic bond is achieved by relying on the appropriate mixed solvent; the stereoselectivity can reach 100%; and the method has a good application prospect in the development of novel drugs and vaccines for resisting Bacillus pyocyaneus and the like.
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Paragraph 0047; 0051
(2019/05/04)
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- Synthesis and Biological Activity of 3,4,-Tri-О-Acetyl-N-Acetylglucosamine and Tetraacetylglucopyranose Conjugated with Alkyl Phosphates
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Abstract: Conjugates of 3,4,6-tri-О-acetyl-N-acetylglucosamine and tetraacetyl glucopyranose with alkyl phosphates were synthesized. The dependence of their antibacterial and antituberculosis activities on the length of the alkyl substituent at the phosphate group was found. The conjugates with a decyl substituent exhibited in vitro the highest antituberculosis activity against Mycobacterium tuberculosis H37Rv (MIC 3?μg/mL) but the weakest effect towards Streptococcus aureus and Bacillus cereus (≤MIC 125 μg/mL). Vice versa, the conjugates with a cetyl substituent demonstrated the highest antibacterial activity in vitro towards S. aureus and B. cereus (MIC 16 μg/mL) but showed the lowest antituberculosis activity (MIC 12 μg/mL) among the compounds under study.
- Sharipova,Garifullin,Sapunova,Voloshina,Kravchenko,Kataev
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p. 155 - 164
(2019/06/14)
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- GLUCOSAMINE DERIVATIVES AND PHARMACEUTICAL USES THEREOF
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There are provided compounds of Formula (A) and pharmaceutically acceptable salts and esters thereof, and pharmaceutical compositions thereof, used for the prevention or treatment in a mammal of joint and bone disorders such as arthritis and osteoporosis.
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Paragraph 0209
(2019/07/03)
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