- Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography
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Solid-phase synthesis is a practical approach for simplifying the time-consuming and routine purification steps in the preparation of numerous naturally occurring molecules; however, studying such reactions is difficult due to the lack of a convenient monitoring method. By using thin-layer chromatography in conjunction with a photolabile linker on a resin, we developed a convenient and simple method for monitoring solid-phase reactions in real time by thin-layer chromatography. This method provides a user-friendly protocol for examining reaction conditions for solid-state syntheses.
- Wu, Chia-Hui,Chen, Chun C.,Lin, Su-Ching,Wang, Cheng-Chung
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Read Online
- Efficient Synthesis of Antigenic Trisaccharides Containing N-Acetylglucosamine: Protection of NHAc as NAc2
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The antigenic trisaccharides, α-gal epitope and H antigen, containing N-acetyl-d-glucosamine (GlcNAc) were synthesized using a diacetyl strategy, in which NHAc is tentatively converted to NAc2 during oligosaccharide construction. Acetylation of
- Tsutsui, Masato,Sianturi, Julinton,Masui, Seiji,Tokunaga, Kento,Manabe, Yoshiyuki,Fukase, Koichi
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Read Online
- Total Synthesis of Nucleoside Antibiotics Plicacetin and Streptcytosine A
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Disaccharide nucleoside antibiotics plicacetin and streptcytosine A (also named rocheicoside A) were effectively synthesized through the common precursor cytosamine. The amosamine and amicetose moieties were efficiently assembled through an α-selective O-
- Fu, Jiqiang,Laval, Stephane,Yu, Biao
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Read Online
- Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts
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Herein, we report the oligopeptide-catalyzed site-selective acylation of partially protected monosaccharides. We identified catalysts that invert site-selectivity compared to N-methylimidazole, which was used to determine the intrinsic reactivity, for 4,6
- Seitz, Alexander,Wende, Raffael C.,Roesner, Emily,Niedek, Dominik,Topp, Christopher,Colgan, Avene C.,McGarrigle, Eoghan M.,Schreiner, Peter R.
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p. 3907 - 3922
(2021/03/09)
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- Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions
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The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.
- Chang, Chun-Wei,Lin, Mei-Huei,Chan, Chieh-Kai,Su, Kuan-Yu,Wu, Chia-Hui,Lo, Wei-Chih,Lam, Sarah,Cheng, Yu-Ting,Liao, Pin-Hsuan,Wong, Chi-Huey,Wang, Cheng-Chung
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supporting information
p. 12413 - 12423
(2021/05/03)
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- Synthesis method of voglibose
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The invention provides a synthesis method of voglibose, and solves the technical problems that in an existing synthesis method of voglibose, raw materials are difficult to obtain, high in price, large in investment, low in yield and not suitable for industrial production. The synthesis method comprises the steps: synthesizing a compound V by taking glucose monohydrate and sodium acetate as raw materials through eleven reaction steps; and preparing a compound VIII from the compound V through an addition reaction, a ring-opening reaction and an aldol condensation reaction, and thus obtaining voglibose through amination reduction of the compound VIII. The synthesis method of voglibose can be widely applied to the technical field of voglibose synthesis methods.
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Paragraph 0060- 0061; 0068-0070
(2021/08/07)
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- Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates
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2-Chloro-1,3-dimethylimidazolinium chloride (DMC, herein also referred to as Shoda's reagent) and its derivatives are useful for numerous synthetic transformations in which the anomeric centre of unprotected reducing sugars is selectively activated in aqueous solution. As such unprotected sugars can undergo anomeric substitution with a range of added nucleophiles, providing highly efficient routes to a range of glycosides and glycoconjugates without the need for traditional protecting group manipulations. This mini-review summarizes the development of DMC and some of its derivatives/analogues, and highlights recent applications for protecting group-free synthesis.
- Fairbanks, Antony J.
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- A Synthetic Carbohydrate-Protein Conjugate Vaccine Candidate against Klebsiella pneumoniae Serotype K2
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Klebsiella pneumoniae causes pneumonia and liver abscesses in humans worldwide and contains virulence factor capsular polysaccharides and lipopolysaccharides linked to the cell wall. Although capsular polysaccharides are good antigens for vaccine producti
- Ravinder, Mettu,Liao, Kuo-Shiang,Cheng, Yang-Yu,Pawar, Sujeet,Lin, Tzu-Lung,Wang, Jin-Town,Wu, Chung-Yi
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p. 15964 - 15997
(2020/11/13)
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- Synthesis of type 1 Lewis b hexasaccharide antigen structures featuring flexible incorporation of l-[U-13C6]-fucose for NMR binding studies
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While 13C-labelled proteins are common tools in NMR studies, lack of access to 13C-labelled carbohydrate structures has restricted their use. l-Fucose is involved in a wide range of physiological and pathophysiological processes in mammalian organisms. He
- Lahmann, Martina,Long, Mark,Ní Cheallaigh, Aisling,Oscarson, Stefan,Reihill, Mark
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supporting information
p. 4452 - 4458
(2020/10/20)
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- One-pot synthesis of cyclic oligosaccharides by the polyglycosylation of monothioglycosides
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Cyclic oligosaccharides such as cyclodextrins (CyDs) have been known as excellent host molecules for the inclusion of various organic guest molecules. The development of new synthetic methods for preparing cyclic oligosaccharides from simple and readily a
- Someya, Hidehisa,Seki, Takehito,Ishigami, Gota,Itoh, Taiki,Saga, Yutaka,Yamada, Yasuyuki,Aoki, Shin
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supporting information
(2019/12/14)
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- Mapping mechanisms in glycosylation reactions with donor reactivity: Avoiding generation of side products
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The glycosylation reaction, which is key for the studies on glycoscience, is challenging due to its complexity and intrinsic side reactions. Thioglycoside is one of the most widely used glycosyl donors in the synthesis of complex oligosaccharides. However, one of the challenges is its side reactions, which lower its yield and limits its efficiency, thereby requiring considerable effort in the optimization process. Herein, we reported a multifaceted experimental approach that reveals the behaviors of side reactions, such as the intermolecular thioaglycon transformation and N-glycosyl succinimides, via the glycosyl intermediate. Our mechanistic proposal was supported by low temperature NMR studies that can further be mapped by utilizing relative reactivity values. Accordingly, we also presented our findings to suppress the generation of side products in solving this particular problem for achieving high-yield glycosylation reactions.
- Wang, Cheng-Chung,Chang, Chun-Wei,Lin, Mei-Huei,Wu, Chia-Hui,Chiang, Tsun-Yi
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p. 15945 - 15963
(2021/01/18)
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- Chondroitin sulfate oligosaccharides and preparation method and applications thereof
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The invention discloses a series of chondroitin sulfate oligosaccharides as shown in a formula and a preparation method and biological activity thereof, and intermediates and a synthesis method of theintermediates. The key points of the invention are as f
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Paragraph 0094; 0102-0104
(2019/08/06)
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- Synthesis of trisaccharide repeating unit of fucosylated chondroitin sulfate
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We described the chemical synthesis of a sulfated trisaccharide repeating unit of fucosylated chondroitin sulfate (FCS), which has significant anticoagulant activity. Well-functionalized monosaccharides were readily prepared, and highly efficient glycosyl
- He, Haiqing,Chen, Dong,Li, Xiaomei,Li, Chengji,Zhao, Jin-Hua,Qin, Hong-Bo
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supporting information
p. 2877 - 2882
(2019/03/21)
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- Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit
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Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.
- Keith, D. Jamin,Townsend, Steven D.
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supporting information
p. 12939 - 12945
(2019/08/22)
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- Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity
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Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.
- Chang, Chun-Wei,Wu, Chia-Hui,Lin, Mei-Huei,Liao, Pin-Hsuan,Chang, Chun-Chi,Chuang, Hsiao-Han,Lin, Su-Ching,Lam, Sarah,Verma, Ved Prakash,Hsu, Chao-Ping,Wang, Cheng-Chung
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supporting information
p. 16775 - 16779
(2019/11/03)
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- Introducing Oxo-Phenylacetyl (OPAc) as a Protecting Group for Carbohydrates
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A series of oxo-phenylacetyl (OPAc)-protected saccharides, with divergent base sensitivity profiles against benzoyl (Bz) and acetyl (Ac) were synthesized, and KHSO5/AcCl in methanol was identified as an easy, mild, selective, and efficient deprotecting reagent for their removal in the perspective of carbohydrate synthesis. Timely monitoring of AcCl reagent was supportive in both sequential and simultaneous deprotecting of OPAc, Bz, and Ac. The salient feature of our method is the orthogonal stability against different groups, its ease to generate different valuable acceptors using designed monosaccharides, and use of OPAc as a glycosyl donar.
- Kumar, Atul,Gannedi, Veeranjaneyulu,Rather, Suhail A.,Vishwakarma, Ram A.,Ahmed, Qazi Naveed
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p. 4131 - 4138
(2019/04/30)
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- COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS
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Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides conjugated to one or more monosaccharide or oligosaccharide moieties. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.
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Page/Page column 191-192
(2018/02/28)
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- Synthesis of Chondroitin Sulfate A Bearing Syndecan-1 Glycopeptide
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Syndecan-1 chondroitin sulfate glycopeptide was synthesized for the first time using the cassette approach. The sequence of glycosylation to form the octasaccharide serine cassette was critical. The glycopeptide was successfully assembled via a 2+ (3 + 3)
- Ramadan, Sherif,Yang, Weizhun,Zhang, Zeren,Huang, Xuefei
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supporting information
p. 4838 - 4841
(2017/09/23)
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- NOVEL NEISSERIA MENINGITIDIS SEROGROUP Y OLIGOMER AND PROCESS FOR SYNTHESIZING THEREOF
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The present invention relates to novel oligomers of Neisseria meningitidis serogroup Y capsular polysaccharide repeating unit (Men-Y oligomers) and process for synthesizing novel Men- Y oligomers. In particular, the present invention relates to the chemic
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Page/Page column 12; 20; 21
(2017/02/24)
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- Oligosaccharide conjugate based on Streptococcus pneumoniae type 3 capsular polysaccharide, preparation method and applications thereof
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The present invention relates to an oligosaccharide conjugate based on Streptococcus pneumoniae type 3 capsular polysaccharide, a preparation method and applications thereof, wherein the structure general formula of the oligosaccharide conjugate is define
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Paragraph 0060; 0061; 0062
(2017/10/13)
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- PREPARATION OF MONOSACCHARIDES, DISACCHARIDES, TRISACCHARIDES, AND PENTASACCHARIDES OF HEPARINOIDS
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The present invention provides preparations of monosaccharides, disaccharides, trisaccharides, and pentasaccharides of heparinoids. The present invention also provides novel monosaccharides, disaccharides, trisaccharides and pentasaccharides for use in th
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Paragraph 0126; 0127
(2017/02/02)
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- Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones
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A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea–hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin functional groups were found to be stable during the oxidation of sulfide.
- Singh, Adesh Kumar,Tiwari, Varsha,Mishra, Kunj Bihari,Gupta, Surabhi,Kandasamy, Jeyakumar
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supporting information
p. 1139 - 1144
(2017/06/20)
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- Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery
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Glycosylated platinum(IV) complexes were synthesized as substrates for GLUTs and OCTs for the first time, and the cytotoxicity and detailed mechanism were determined in vitro and in vivo. Galactoside Pt(IV), glucoside Pt(IV), and mannoside Pt(IV) were highly cytotoxic and showed specific cancer-targeting properties in vitro and in vivo. Glycosylated platinum(IV) complexes 5, 6, 7, and 8 (IC50 0.24-3.97 μM) had better antitumor activity of nearly 166-fold higher than the positive controls cisplatin (1a), oxaliplatin (3a), and satraplatin (5a). The presence of a hexadecanoic chain allowed binding with human serum albumin (HSA) for drug delivery, which not only enhanced the stability of the inert platinum(IV) prodrugs but also decreased their reduction by reductants present in human whole blood. Their preferential accumulation in cancer cells compared to noncancerous cells (293T and 3T3 cells) suggested that they were potentially safe for clinical therapeutic use.
- Ma, Jing,Wang, Qingpeng,Huang, Zhonglv,Yang, Xiande,Nie, Quandeng,Hao, Wenpei,Wang, Peng George,Wang, Xin
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supporting information
p. 5736 - 5748
(2017/07/22)
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- Efficient Divergent Synthesis of New Immunostimulant 4″-Modified α-Galactosylceramide Analogues
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A synthesis strategy for the swift generation of 4″-modified α-galactosylceramide (α-GalCer) analogues is described, establishing a chemical platform to comprehensively investigate the structure-activity relationships (SAR) of this understudied glycolipid
- Janssens, Jonas,Decruy, Tine,Venken, Koen,Seki, Toshiyuki,Krols, Simon,Van Der Eycken, Johan,Tsuji, Moriya,Elewaut, Dirk,Van Calenbergh, Serge
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p. 642 - 647
(2017/06/13)
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- Determining Substrate Specificities of β1,4-Endogalactanases Using Plant Arabinogalactan Oligosaccharides Synthesized by Automated Glycan Assembly
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Pectin is a structurally complex plant polysaccharide with many industrial applications in food products. The structural elucidation of pectin is aided by digestion assays with glycosyl hydrolases. We report the automated glycan assembly of oligosaccharid
- Bartetzko, Max P.,Schuhmacher, Frank,Seeberger, Peter H.,Pfrengle, Fabian
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supporting information
p. 1842 - 1850
(2017/02/10)
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- Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3
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Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.
- Weng, Shiue-Shien,Hsieh, Kun-Yi,Zeng, Zih-Jian
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p. 464 - 473
(2017/05/19)
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- Total synthesis of mangiferin, homomangiferin, and neomangiferin
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Total synthesis of mangiferin, homomangiferin, and neomangiferin, three C-glycosyl xanthone natural products with a wide spectrum of pharmacological effects, has been achieved starting from 2,3,4,6-tetra-O-benzyl-α/β-d-glucopyranose. The key steps involve a stereoselective Lewis acid promoted C-glycosylation of protected phloroglucinol with tetrabenzylglucopyranosyl acetate and a highly regioselective base-induced cyclization for the construction of the core xanthone skeleton.
- Wei, Xiong,Liang, Danlin,Wang, Qing,Meng, Xiangbao,Li, Zhongjun
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supporting information
p. 8821 - 8831
(2016/10/03)
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- HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS
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Glycosphingolipids (GSLs) compositions and methods for iNKT-independent induction of chemokines are disclosed.
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Paragraph 0242
(2016/05/10)
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- An investigation of construction of chondroitin sulfate E (CS-E) repeating unit
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A series of the derivatives of chondroitin sulfate E (CS-E) disaccharide repeating unit were prepared by postglycosylation–oxidation strategy. The strategy showed excellent performance in glycosylation both on the reactivity and stereoselectivity. Different protecting methodologies were used for the manipulation of disaccharide building blocks. Substitutes at C-4 of glucosyl donors mildly influenced the glycosylation. The current synthesis afforded a feasible approach for the preparation of CS-E repeating unit.
- Yang, Shuang,Wang, A-peng,Zhang, Guangyan,Di, Xiangjie,Zhao, Zhehui,Lei, Pingsheng
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supporting information
p. 5659 - 5670
(2016/08/23)
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- TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
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The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.
- Hsu, Mei-Yuan,Liu, Yi-Pei,Lam, Sarah,Lin, Su-Ching,Wang, Cheng-Chung
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supporting information
p. 1758 - 1764
(2016/10/05)
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- A Kinsenoside and GoodyerosideA analogs of the preparation and use thereof
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The invention discloses a preparation method and application of compounds as shown in formula I and II, and in particular relates to preparation of Kinsenoside or GoodyerosideA analogue and medical application of the Kinsenoside or GoodyerosideA analogue
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Paragraph 0040; 0041; 0042; 0043; 0044
(2017/06/14)
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- HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS WITH ALTERED GLYCOSYL GROUPS
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Glycosphingolipids (GSLs) bearing α-glucose (α-Glc) that preferentially stimulate human invariant NKT (iNKT) cells are provided. GSLs with α-glucose (α-Glc) that exhibit stronger induction in humans (but weaker in mice) of cytokines and chemokines and exp
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Paragraph 0243; 0246; 0247
(2015/03/16)
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- Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4'-deoxy-4'-fluoro-Thomsen-Friedenreich epitope
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The development of selective anticancer vaccines that provide enhanced protection against tumor recurrence and metastasis has been the subject of intense research in the scientific community. The tumor-associated glycoprotein MUC1 represents a well-established target for cancer immunotherapy and has been used for the construction of various synthetic vaccine candidates. However, many of these vaccine prototypes suffer from an inherent low immunogenicity and are susceptible to rapid in vivo degradation. To overcome these drawbacks, novel fluorinated MUC1 glycopeptide-BSA/TTox conjugate vaccines have been prepared. Immunization of mice with the 4'F-TF-MUC1-TTox conjugate resulted in strong immune responses overriding the natural tolerance against MUC1 and producing selective IgG antibodies that are cross-reactive with native MUC1 epitopes on MCF-7 human cancer cells.
- Johannes, Manuel,Reindl, Maximilian,Gerlitzki, Bastian,Schmitt, Edgar,Hoffmann-R?der, Anja
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supporting information
p. 155 - 161
(2015/02/05)
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- Automated Glycan Assembly of Oligosaccharides Related to Arabinogalactan Proteins
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Arabinogalactan proteins are heavily glycosylated proteoglycans in plants. Their glycan portion consists of type-II arabinogalactan polysaccharides whose heterogeneity hampers the assignment of the arabinogalactan protein function. Synthetic chemistry is
- Bartetzko, Max P.,Schuhmacher, Frank,Hahm, Heung Sik,Seeberger, Peter H.,Pfrengle, Fabian
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supporting information
p. 4344 - 4347
(2015/09/15)
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- Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature
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A general and efficient protocol for the palladium-catalyzed functionalization of mono- and polyglycosyl thiols by using the palladacycle precatalyst G3-XantPhos was developed. The C-S bond-forming reaction was achieved rapidly at room temperature with various functionalized (hetero)aryl-, alkenyl-, and alkynyl halides. The functional group tolerance on the electrophilic partner is typically high and anomer selectivities of thioglycosides are high in all cases studied. New sulfur nucleophiles such as thiophenols, alkythiols, and thioaminoacids (cysteine) were also successfully coupled to lead to the most general and practical method yet reported for the functionalization of thiols.
- Bruneau, Alexandre,Roche, Maxime,Hamze, Abdallah,Brion, Jean-Daniel,Alami, Mouad,Messaoudi, Samir
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p. 8375 - 8379
(2015/06/02)
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- Exploring glycosylation reactions under continuous-flow conditions
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The industrial development of carbohydrate-based drugs is greatly thwarted by the typical challenges inherent in oligosaccharide synthesis. The practical advantages of continuous-flow synthesis in microreactors (high reproducibility, easy scalability, and fast reaction optimization) may offer an effective support to make carbohydrates more attractive targets for drug-discovery processes. Here we report a systematic exploration of the glycosylation reaction carried out under microfluidic conditions. Trichloroacetimidates and thioglycosides have been investigated as glycosyl donors, using both primary and secondary acceptors. Each microfluidic glycosylation has been compared with the corresponding batch reaction, in order to highlight advantages and drawbacks of microreactors technology. As a significant example of multistep continuous-flow synthesis, we also describe the preparation of a trisaccharide by means of two consecutive glycosylations performed in interconnected microreactors.
- Cancogni, Damiano,Lay, Luigi
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supporting information
p. 2873 - 2878
(2015/01/16)
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- Fluorous-assisted chemoenzymatic synthesis of heparan sulfate oligosaccharides
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The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag attached at the reducing end is reported. The fluorous tert-butyl dicarbonate (FBoc) tag did not interfere with enzymatic recognition
- Cai, Chao,Dickinson, Demetria M.,Li, Lingyun,Masuko, Sayaka,Suflita, Matt,Schultz, Victor,Nelson, Shawn D.,Bhaskar, Ujjwal,Liu, Jian,Linhardt, Robert J.
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supporting information
p. 2240 - 2243
(2014/05/06)
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- Synthesis of a poly-hydroxypyrolidine-based inhibitor of Mycobacterium tuberculosis GlgE
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(Chemical Equation Presented). Long treatment times, poor drug compliance, and natural selection during treatment of Mycobacterium tuberculosis (Mtb) have given rise to extensively drug-resistant tuberculosis (XDR-TB). As a result, there is a need to iden
- Veleti, Sri Kumar,Lindenberger, Jared J.,Thanna, Sandeep,Ronning, Donald R.,Sucheck, Steven J.
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p. 9444 - 9450
(2015/02/19)
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- Synthesis of oligomeric mannosides and their structure-binding relationship with concanavalin A
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Small glycodendrimers with α-mannosyl ligands were synthesized by using copper-catalyzed azide-alkyne coupling chemistry and some of these molecules were used as multivalent ligands to study the induction of concanavalin A (Con A) precipitation. The results showed that the monovalent mannose ligand could induce the precipitation of Con A. This unexpected finding initiated a series of studies to characterize the molecular basis of the ligand-lectin interaction. The atypical precipitation is found to be specific to the mannose, fluorescein moiety (FITC), and Con A. Apparently the mannose ligand binds to Con A through hydrogen-bonding interactions, whereas the binding of FITC is mediated by hydrophobic forces. Being precipitate: A series of glycodendrimers with α-mannosyl ligands were prepared and used to explore the precipitation of concanavalin A (Con A). Surprisingly, the monovalent mannose ligand induced Con A precipitation, which led to an investigation of the molecular basis of the ligand-lectin interaction (see figure).
- Li, Chen-Wei,Hon, Kai-Wei,Ghosh, Bhaswati,Li, Po-Han,Lin, Hsien-Ya,Chan, Po-Han,Lin, Chun-Hung,Chen, Yu-Chie,Mong, Kwok-Kong Tony
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supporting information
p. 1786 - 1796
(2014/07/08)
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- CARBOHYDRATE-MODIFIED GLYCOPROTEINS AND USES THEREOF
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The present invention provides immunogenic compounds which stimulate immune responses in a subject. The present invention provides compositions comprising an isolated glycoprotein antigen covalently bound at pre-existing carbohydrate residues present on the glycoprotein to a carbohydrate epitope. The present invention also provides a method to induce an immune response in a subject comprising administering the compounds of the invention. The present invention further provides methods of making the compounds of the invention and methods of using the compounds of the invention to stimulate immune responses to infectious disease agents and tumors.
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Paragraph 0115-0117
(2014/10/04)
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- Synthesis and characterization of sulfated gal-β-1,3/4-GlcNAc disaccharides through consecutive protection/glycosylation steps
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We have developed an expeditious procedure to yield large amounts of orthogonally protected Gal-β1,3/4-GlcNAc, which allowed for the systematic introduction of a sulfate group onto the C3/C6 positions of Gal and/or the C6 position of GlcNAc. In particular
- Tu, Zhijay,Hsieh, Hsiao-Wu,Tsai, Chih-Ming,Hsu, Chia-Wei,Wang, Shy-Guey,Wu, Kuan-Jung,Lin, Kuo-I,Lin, Chun-Hung
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supporting information
p. 1536 - 1550
(2013/07/26)
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- Regiospecific anomerisation of acylated glycosyl azides and benzoylated disaccharides by using TiCl4
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Chelation induced anomerisation is promoted when Lewis acids, such as TiCl4 or SnCl4, coordinate to the pyranose ring oxygen atom and another site, giving rise to endocyclic cleavage and isomerisation to the more stable anomer. In this research regiospecific site-directed anomerisation is demonstrated. TiCl4 (2.5equiv) was employed to induce anomerisation of 15 glycosyl azide and disaccharide substrates of low reactivity, and high yields (>75 %) and stereoselectivies (α/β>9:1) were achieved. The examples included glucopyranuronate, galactopyranuronate and mannopyranuronate as well as N-acetylated glucopyranuronate and galactopyranuronate derivatives. A disaccharide with the α1→4 linkage found in polygalacturonan was included. The use of benzoylated saccharides was found to be important in disaccharide anomerisation as attempts to isomerise related acetyl protected and 2,3-carbonate protected derivatives were not successful. Copyright
- Farrell, Mark,Zhou, Jian,Murphy, Paul V.
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supporting information
p. 14836 - 14851
(2013/11/06)
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- METHODS AND INTERMEDIATES FOR THE PREPARATION OF FONDAPARINUX
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The present invention relates to methods for the synthesis of fondaparinux and intermediates thereto.
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Paragraph 00188; 00189
(2014/01/08)
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- Chemical synthesis of a heparan sulfate glycopeptide: Syndecan-1
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Finishing first: The highly complex structure of the title compound (see picture) was assembled. The protective groups utilized, as well as the sequences for formation of the glycosyl linkages and protecting group removal are critical to the success of the synthesis. This first preparation of a heparan sulfate glycopeptide lays the foundation for accessing other members of this class of molecules. Copyright
- Yang, Bo,Yoshida, Keisuke,Yin, Zhaojun,Dai, Hang,Kavunja, Herbert,El-Dakdouki, Mohammad H.,Sungsuwan, Suttipun,Dulaney, Steven B.,Huang, Xuefei
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supporting information
p. 10185 - 10189,5
(2012/12/12)
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- Chemoselective deacylation of functionalized esters catalyzed by dioxomolybdenum dichloride
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Among five different oxidometallic species and two Lewis acids investigated, MoO2Cl2 shows the best catalytic and chemoselective activity for the deacylation of esters in methanol at ambient or elevated temperature. Both high efficiency and chemoselectivity were achieved for substrates bearing different ether or ester groups. Acylated mono and disaccharides can also be selectively deacetylated in good yields, leading to useful carbohydrate templates for further synthetic manipulations.
- Liu, Cheng-Yuan,Chen, Hui-Ling,Ko, Chih-Min,Chen, Chien-Tien
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experimental part
p. 872 - 876
(2011/03/19)
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- SYNTHETIC OLIGOSACCHARIDES FOR MORAXELLA VACCINE
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The present invention provides synthetic Moraxella catarrhalis lipooligosaccharide (LOS)-based oligosaccharides and conjugates containing various M. catarrhalis serotype-specific oligosaccharide antigens or various core M. catarrhalis oligosaccharide structures or motifs corresponding to one or more of the three major serotypes and/or members within a given serotype. The oligosaccharides may be synthesized by a chemical assembly methodology relying on a limited number of monosaccharide and disaccharide building blocks. The invention further provides M. catarrhalis LOS-based immunogenic and immunoprotective compositions and antibodies derived therefrom for diagnosing, treating, and preventing infections caused by M. catarrhalis.
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Page/Page column 51
(2011/11/13)
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- Ultrasonication-assisted spray ionization mass spectrometry for on-line monitoring of organic reactions
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A straightforward on-line monitoring of organic reactions by ultrasonication-assisted spray ionization mass spectrometry (UASI MS) is demonstrated in this work.
- Chen, Tsung-Yi,Chao, Chin-Sheng,Mong, Kwok-Kong Tony,Chen, Yu-Chie
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supporting information; experimental part
p. 8347 - 8349
(2011/02/16)
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- Synthesis and applications of a light-fluorous glycosyl donor
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A new method using a light-fluorous glycosyl donor and an orthogonal tagging strategy to synthesize oligosaccharides and glycoconjugates has been developed. The glycosyl donor orthogonally protected with a C8F 17-Silyl tag and benzoyl groups was reacted with excess amounts of glycosyl acceptor. Fluorous solid-phase extraction separated the glycosylated product and unreacted glycosyl acceptor. This new protocol has high reaction efficiency and easy separation, which was demonstrated in the synthesis of an unprotected trisaccharide and an O-glycosylated serine in this paper.
- Zhang, Fa,Zhang, Wei,Zhang, Yan,Curran, Dennis P.,Liu, Gang
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supporting information; experimental part
p. 2594 - 2597
(2009/08/07)
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- Low-concentration 12-trans β-selective glycosylation strategy and its applications in oligosaccharide synthesis
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This study develops an operationally easy, efficient, and general 1,2-trans β-selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent β-selectivities in glycosylation reactions. This method is widely applicable to a range of glycosyl substrates irrespective of their structures and hydroxyl-protecting functions. This low-concentration 1,2-trans β-selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2-trans β-glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant β-(1-6)-glucan trisaccharide, β-linked Gb3 and isoGb3 derivatives.
- Chao, Chin-Sheng,Li, Chen-Wei,Chen, Min-Chun,Chang, Shih-Sheng,Mong, Kwok-Kong Tony
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supporting information; experimental part
p. 10972 - 10982
(2010/04/30)
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- Direct transformation of unprotected sugars to aryl 1-thio-β- glycosides in aqueous media using 2-chloro-l, 3-dimethylimidazolinium chloride
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Aryl 1-thioglycosides have directly been synthesized in good yields from the corresponding unprotected sugars and thiols without protection of the hydroxy groups by using 2-chloro-l, 3-dimethylirnidazolinium chloride (DMC) as dehydrative condensing agent.
- Tanaka, Tomonari,Matsumoto, Takeshi,Noguchi, Masato,Kobayashi, Atsushi,Shoda, Shin-Ichiro
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supporting information; experimental part
p. 458 - 459
(2010/03/04)
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