- TARGETED PLASMA PROTEIN DEGRADATION
-
The present invention is directed to the bifunctional compounds and the use of such bifunctional compounds to lower plasma levels of extracellular target molecules by lysosomal degradation. Such bifunctional compounds have a cell surface receptor ligand covalently linked to a ligand that is capable of binding to an extracellular target molecule (such as a ligand for a growth factor, a cytokine, a chemokine, a hormone, a neurotransmitter, a capsid, a soluble receptor, an extracellular secreted protein, an antibody, a lipoprotein, an exosome, a virus, a cell, or a plasma membrane protein), where the cell surface receptor is associated with receptor mediated endocytosis, including asialoglycoprotein receptor (ASGPR) mediated lysosomal degradation and mannose-6-phosphate (M6PR) mediated lysosomal degradation. Pharmaceutical compositions comprising such bifunctional compounds and methods of treating a disease or disorder mediated by an extracellular molecule using such bifunctional compounds are also provided herein.
- -
-
Page/Page column 172; 175-176
(2021/08/14)
-
- Efficient and reproducible synthesis of an Fmoc-protected Tn antigen
-
This concise total synthesis of the Thomsen-Nouveau (Tn) glycoconjugate was accomplished using a palladium-catalyzed coupling between the glycosyl donor and Fmoc-protected serine acceptor. This is, to the best of our knowledge, the shortest synthesis reported from galactose for preparing this essential building block for large-scale solid phase peptide synthesis.
- Chapa-Villarreal, Fabiola A.,Chiaramonte, Jonathan,Piazza, Sabrina M.,Reynolds, Michael R.,Trant, John F.,Xu, Peihan
-
p. 19224 - 19227
(2021/11/09)
-
- Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement
-
Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.
- Jiang, Xuefeng,Li, Jiagen,Wang, Ming
-
supporting information
p. 9053 - 9057
(2021/11/30)
-
- TARGETED BIFUNCTIONAL DEGRADERS
-
The present invention provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In another aspect, the present invention provides bifunctional compounds that can be used to promote or enhance degradation of certain autoantibodies. In certain embodiments, treatment or management of a disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein or the autoantibody in the subject. Thus, in certain embodiments, administration of a compound of the invention to the subject removes or reduces the circulation concentration of the circulating protein or the autoantibody, thus treating, ameliorating, or preventing the disease and/or disorder. In certain embodiments, the circulating protein is TNF.
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-
Page/Page column 157
(2021/04/17)
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- ENGINEERED ANTIBODIES AS MOLECULAR DEGRADERS THROUGH CELLULAR RECEPTORS
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The present disclosure provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In certain embodiments, the circulating protein mediates a disease and/or disorder in a subject, and treatment or management of the disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein in the subject. Thus, in certain embodiments, administration of a compound of the disclosure to the subject removes or reduces the circulation concentration of the circulating protein, thus treating, ameliorating, or preventing the disease and/or disorder.
- -
-
Page/Page column 3; 77
(2021/04/17)
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- Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34
-
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.
-
-
- Positional Scanning MUC1 Glycopeptide Library Reveals the Importance of PDTR Epitope Glycosylation for Lectin Binding
-
One of the main barriers to explaining the functional significance of glycan-based changes in cancer is the natural epitope heterogeneity found on the surface of cancer cells. To help address this knowledge gap, we focused on designing synthetic tools to explore the role of tumor-associated glycans of MUC1 in the formation of metastasis via association with lectins. In this study, we have synthesized for the first time a MUC1-derived positional scanning synthetic glycopeptide combinatorial library (PS-SGCL) that vary in number and location of cancer-associated Tn antigen using the "tea bag" approach. The determination of the isokinetic ratios necessary for the equimolar incorporation of (glyco)amino acids mixtures to resin-bound amino acid was determined, along with developing an efficient protocol for on resin deprotection of O-acetyl groups. Enzyme-linked lectin assay was used to screen PS-SGCL against two plant lectins, Glycine max soybean agglutinin and Vicia villosa. The results revealed a carbohydrate density-dependent affinity trend and site-specific glycosylation requirements for high affinity binding to these lectins. Hence, PS-SGCLs provide a platform to systematically elucidate MUC1-lectin binding specificities, which in the long term may provide a rational design for novel inhibitors of MUC1-lectin interactions involved in tumor spread and glycopeptide-based cancer vaccines.
- Singh, Yashonandini,Rodriguez Benavente, Maria C.,Al-Huniti, Mohammed H.,Beckwith, Donella,Ayyalasomayajula, Ramya,Patino, Eric,Miranda, William S.,Wade, Alex,Cudic, Maré
-
p. 1434 - 1445
(2020/01/02)
-
- Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals
-
A novel synthetic route for highly substituted conjugated ketones has been developed utilizing glycals as starting materials. The two-step process combined the Heck reaction/Lewis acid promoted ring opening to afford the products in 33–80 % overall yields and with a high level of trans stereoselectivity. Since the products are essentially the aldols, this methodology may be employed in some cases as an alternative synthetic route to the typical aldol condensation. Densely substituted, selectively protected conjugated ketones are synthetically attractive structures which, in our case, proved to be biologically equally appealing. Namely, they showed activity against several cancer cell lines, such as HeLa, K562, MDA-MB-453, in some instances overperforming cisplatin used as a standard.
- Jovanovic, Predrag,Petkovic, Milos,Simic, Milena,Jovanovic, Milos,Tasic, Gordana,Crnogorac, Marija Djordjic,Zizak, Zeljko,Savic, Vladimir
-
p. 4701 - 4709
(2019/07/31)
-
- Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP)
-
Antifreeze glycoproteins are a class of biological agents which enable living at temperatures below the freezing point of the body fluids. Antifreeze glycopeptides usually consist of repeating tripeptide unit (-Ala-Ala-Thr?-), glycosylated at the threonine side chain. However, on the microscopic level, the mechanism of action of these compounds remains unclear. As previous research has shown, antifreeze activity of antifreeze glycopeptides strongly relies on the overall conformation of the molecule as well an on the stereochemistry of amino acid residues. The desired monoglycosylated analogues with acetylated amino termini and the carboxy termini in form of N-methylamide have been synthesized. Conformational nuclear magnetic resonance (NMR) studies of the designed analogues have shown a strong influence of the stereochemistry of amino acid residues on the peptide chain stability, which could be connected to the antifreeze activity of these compounds. A better understanding of the mechanism of action of antifreeze glycopeptides would allow applying these materials, e.g., in food industry and biomedicine.
- Urbańczyk, Ma?gorzata,Jewgiński, Micha?,Krzciuk-Gula, Joanna,Góra, Jerzy,Latajka, Rafa?,Sewald, Norbert
-
supporting information
p. 1581 - 1591
(2019/08/07)
-
- Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity
-
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
-
p. 16775 - 16779
(2019/11/03)
-
- BI-FUNCTIONAL MOLECULES TO DEGRADE CIRCULATING PROTEINS
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The present invention is directed to bi-functional compounds which find use as pharmaceutical agents in the treatment of disease states and/or conditions which are through.macrophage migration inhibitory factor (MIF) or immunoglubin G (IgG). The present invention is also directed to pharmaceutical compositions which comprise these bi- functional compounds as well as methods for treating disease states and/or conditions which are mediated through MIF/lgG or where MIF/lgG is a contributing factor to the development and perpetuation of diseases and/or conditions, especially including autoimmune diseases and cancer, among others. The purpose of the present invention is to provide a molecular strategy to lower plasma MIF/lgG level in patients with autoimmune diseases or certain types of cancers. The b.i -functional molecule construct is comprised of a MIF/IgQ-targeting motif, that is derived from small molecule MIF/lgG ligands, and an ASGPr- targeting motif that binds to hepatocyte asialoglycoprotein receptor { ASGPr). The compounds selectively bind MIF or IgG in plasma and subsequently engage the endo-lysosomal pathway of hepatocytes through ASGPr. As a consequence, MIF/igG is internalized and degraded by hepatocytes, thus resulting in potential attenuation of corresponding disease symptoms which are modulated through MIF/igG.
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Page/Page column 85-86
(2019/11/04)
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- Method for stereoselectively synthesizing beta-2-deoxyglycoside bond
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The invention discloses a method for stereoselectively synthesizing a beta-2-deoxyglycoside bond. The method comprises the following steps: performing glycosylation on 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene serving as a donor, a saccharide receptor and a molecular sieve under the condition of the existence of an accelerant, wherein an isopropyl acetal protectivegroup is mounted on a 3-site hydroxyl and a 4-site hydroxyl of the 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene and a TBDPS is mounted on the 6-site of the 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene; through the synergistic effect of the protective groups, sugar ring conformation of the donor is controlled, and the stereoselective synthesis of a beta-configuration is realized. According to the method, the stereoselectivity of the glycosylation can be controlled effectively and stereoselectively; the method is wide in substrate application range and convenient to operate; raw materials are easy to obtain; side reactions of the glycosylation are few; a target product is high in yield and optical purity; a new design thought is provided for the research of the glycosylation.
- -
-
Paragraph 0031-0032; 0036
(2019/07/04)
-
- Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit
-
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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p. 12939 - 12945
(2019/08/22)
-
- Design and synthesis of trivalent Tn glycoconjugate polymers by nitroxide-mediated polymerization
-
A new synthetic method for preparing Tn glycoconjugate polymers, containing tumor-associated carbohydrate antigens, by controlled living radical polymerization is reported. To mimic the authentic structures of Tn glycopeptide antigens and to explore the controlled living radical polymerization, three tumor-associated carbohydrate antigens (GalNAc, GalNAcα1-O-Ser, and GalNAcα1-O-Thr) were attached to a styrene-type monomer through a diethylene glycol spacer. Under nitroxide-mediated polymerization, controlled living radical polymerization proceeded to afford defined glycopeptide polymers with different Tn densities and compositions. The polydispersity index (PDI) and molecular weights were increased and conversions were decreased upon increasing the concentration of Tn glycoconjugate monomers. The resulting Tn glycoconjugate polymers were characterized by NMR and IR. The spectral data indicate that the Tn glycoconjugate moiety did attach to the polymer chain and Tn glycoconjugate density could be adjusted through the nitroxide-mediated polymerization conditions. The number of Tn units containing in the polymer chains could be estimated by NMR integration. This synthetic approach provides a new and efficient tool for constructing novel Tn glycoconjugate polymers.
- Liu, Si-Xian,Tsai, Yun-Tzu,Lin, Yu-Tung,Li, Jia-Yue,Chang, Che-Chien
-
-
- Stereoselective Synthesis of Fluorinated Galactopyranosides as Potential Molecular Probes for Galactophilic Proteins: Assessment of Monofluorogalactoside–LecA Interactions
-
The replacement of hydroxyl groups by fluorine atoms on hexopyranoside scaffolds may allow access to invaluable tools for studying various biochemical processes. As part of ongoing activities toward the preparation of fluorinated carbohydrates, a systematic investigation involving the synthesis and biological evaluation of a series of mono- and polyfluorinated galactopyranosides is described. Various monofluorogalactopyranosides, a trifluorinated, and a tetrafluorinated galactopyranoside have been prepared using a Chiron approach. Given the scarcity of these compounds in the literature, in addition to their synthesis, their biological profiles were evaluated. Firstly, the fluorinated compounds were investigated as antiproliferative agents using normal human and mouse cells in comparison with cancerous cells. Most of the fluorinated compounds showed no antiproliferative activity. Secondly, these carbohydrate probes were used as potential inhibitors of galactophilic lectins. The first transverse relaxation-optimized spectroscopy (TROSY) NMR experiments were performed on these interactions, examining chemical shift perturbations of the backbone resonances of LecA, a virulence factor from Pseudomonas aeruginosa. Moreover, taking advantage of the fluorine atom, the 19F NMR resonances of the monofluorogalactopyranosides were directly monitored in the presence and absence of LecA to assess ligand binding. Lastly, these results were corroborated with the binding potencies of the monofluorinated galactopyranoside derivatives by isothermal titration calorimetry experiments. Analogues with fluorine atoms at C-3 and C-4 showed weaker affinities with LecA as compared to those with the fluorine atom at C-2 or C-6. This research has focused on the chemical synthesis of “drug-like” low-molecular-weight inhibitors that circumvent drawbacks typically associated with natural oligosaccharides.
- Denavit, Vincent,Lainé, Danny,Bouzriba, Chahrazed,Shanina, Elena,Gillon, émilie,Fortin, Sébastien,Rademacher, Christoph,Imberty, Anne,Giguère, Denis
-
supporting information
p. 4478 - 4490
(2019/03/07)
-
- Controlled Living Cascade Polymerization to Make Fully Degradable Sugar-Based Polymers from d -Glucose and d -Galactose
-
Monomers derived from glucose and galactose, which contain an endocyclic alkene (in the sugar ring) and a terminal alkyne, underwent a cascade polymerization to prepare new polymers with the ring-opened sugar incorporated into the polymer backbone. Polymerizations were well-controlled, as demonstrated by a linear increase in molecular weight with monomer-to-initiator ratio and generally narrow molecular weight dispersity values. The living nature of the polymerization was supported by the preparation of a block copolymer from two different sugar-based monomers. The resulting polymers were also fully degradable. They underwent fast and complete depolymerization to small molecules under acidic conditions.
- Bhaumik, Atanu,Peterson, Gregory I.,Kang, Cheol,Choi, Tae-Lim
-
supporting information
p. 12207 - 12211
(2019/08/20)
-
- BIFUNCTIONAL SMALL MOLECULES TO TARGET THE SELECTIVE DEGRADATION OF CIRCULATING PROTEINS
-
The present invention is directed to bifunctional small molecules which contain a circulating protein binding moiety (CPBM) linked through a linker group to a cellular receptor binding moiety (CRBM) which is a membrane receptor of degrading cell such as a hepatocyte or other degrading cell. In embodiments, the (CRBM) is a moiety which binds to asialoglycoprotein receptor (an asialoglycoprotein receptor binding moiety, or ASGPRBM) of a hepatocyte. In additional embodiments, the (CRBM) is a moiety which binds to a receptor of other cells which can degrade proteins, such as a LRP1, LDLR, FcyRI, FcRN, Transferrin or Macrophage Scavenger receptor. Pharmaceutical compositions based upon these bifunctional small molecules represent an additional aspect of the present invention. These compounds and/or compositions may be used to treat disease states and conditions by removing circulating proteins through degradation in the hepatocytes or macrophages of a patient or subject in need of therapy. Methods of treating disease states and/or conditions in which circulating proteins are associated with the disease state and/or condition are also described herein.
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Page/Page column 70; 91
(2019/11/04)
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- Sugar amino acids and oligosaccharide mimic prepared from sugar amino acids
-
Belonging to the field of carbohydrate chemistry, the invention in particular relates to sugar amino acids and an oligosaccharide mimic prepared from the same. Cheap and easily available D-glucose andD-galactose are adopted as the starting raw materials for a series of reactions to obtain all-benzyl-protected glycal, the latter undergoes one-step free radical addition under the action of ceric ammonium nitrate (CAN) to obtain a precursor 2-C-nitro compound of SAAs, then Pd/C hydrogenation reaction for deprotection of Bn, reductive ammoniation and selective Boc protection reaction are carriedout to obtain a protected intermediate product of amino; then TIPSCl is utilized for selective protection of C-6 hydroxyl, then C-3 hydroxyl and C-4 hydroxyl are subjected to Bn protection, and deprotection of TIPS is carried out on C-6 hydroxyl; finally the C-6 hydroxyl is oxidized to obtain glucose-type and galactose-type SAAs blocks; and based on the obtained SAAs, a straight-chain type oligosaccharide mimic connected by an amido bond is synthesized, and condensation reaction is carried out to obtain 9 homologous and heterologous oligosaccharide mimics of straight-chain dimer, tetramer andoctamer. The method is simple, convenient, fast and effective.
- -
-
Paragraph 0074; 0076; 0079
(2018/10/04)
-
- Synthetic MUC1 antitumor vaccine with incorporated 2,3-sialyl-T carbohydrate antigen inducing strong immune responses with isotype specificity
-
The endothelial glycoprotein MUC1 is known to underlie alterations in cancer by means of aberrant glycosylation accompanied by changes in morphology. The heavily shortened glycans induce a collapse of the peptide backbone and enable accessibility of the latter to immune cells, rendering it a tumor-associated antigen. Synthetic vaccines based on MUC1 tandem repeat motifs, comprising tumor-associated 2,3-sialyl-T antigen, conjugated to the immunostimulating tetanus toxoid, are reported herein. Immunization with these vaccines in a simple water/oil emulsion produced a strong immune response in mice to which stimulation with complete Freund’s adjuvant (CFA) was not superior. In both cases, high levels of IgG1 and IgG2a/b were induced in C57BL/6 mice. Additional glycosylation in the immunodominant PDTRP domain led to improved binding of the induced antisera to MCF-7 breast tumor cells, compared with that of the monoglycosylated peptide vaccine.
- Stra?burger, David,Glaffig, Markus,Stergiou, Natascha,Bialas, Sabrina,Besenius, Pol,Schmitt, Edgar,Kunz, Horst
-
p. 1142 - 1146
(2018/10/21)
-
- Reengineering Chemical Glycosylation: Direct, Metal-Free Anomeric O-Arylation of Unactivated Carbohydrates
-
To sustain innovation in glycobiology, effective routes to well-defined carbohydrate probes must be developed. For over a century, glycosylation has been dominated by the formation of the anomeric Csp3?O acetal junction in glycostructures. A dissociative mechanistic spectrum spanning SN1 and SN2 is frequently operational thereby reducing the efficiency. By reengineering this fundamental process, an orthogonal disconnection allows the acetal to be formed directly from the reducing sugar without the need for substrate pre-functionalisation. The use of stable aryliodonium salts facilitates a formal O?H functionalisation reaction. This allows lactols to undergo mild, metal-free O-arylation at ambient temperature. The efficiency of the transformation has been validated using a variety of pyranoside and furanoside monosaccharides in addition to biologically relevant di- and trisaccharides (up to 85 %). Fluorinated mechanistic probes that augment the anomeric effect were employed. It is envisaged that this strategy will prove expansive for the construction of complex acetals under substrate-based stereocontrol.
- Lucchetti, Nicola,Gilmour, Ryan
-
p. 16266 - 16270
(2018/10/24)
-
- General Approach to Five-Membered Nitrogen Heteroaryl C-Glycosides Using a Palladium/Copper Cocatalyzed C-H Functionalization Strategy
-
A general approach to the synthesis of diverse heteroaryl-C-Δ1,2-glycosides has been developed by employing the Pd(OAc)2/CuI cocatalyzed direct cross-coupling of five-membered nitrogen heterocycles with 1-iodoglycals in a C-H activation manner. Using this method, 27 examples of heteroaryl-C-Δ1,2-glycosides, containing indoles, thiazoles, benzothiazoles, imidazoles, benzimidazoles, and benzoxazoles as aglycones were obtained in 43-99% yield.
- Zhang, Shuo,Niu, You-Hong,Ye, Xin-Shan
-
supporting information
p. 3608 - 3611
(2017/07/15)
-
- Substrate-Controlled Diastereoselective Synthesis of Sugar-Based Chlorinated Perhydrofuro[2,3-b]pyrans via Copper(I)-Catalyzed Radical Cyclization
-
The work describes the first copper(I) chloride/2,2′-bipyridine-catalyzed atom transfer radical cyclization (ATRC) of unsaturated carbohydrate-derived chloroacetals to generate chlorinated perhydrofuro[2,3-b]pyrans via an effective diastereoselective route. Various glycals (glucal, galactal and lactal) underwent the Ferrier rearrangement with 2,2,2-trichloroethanols to give acetal precursors stereoselectively, R-selective with galactal in contrast to S-selective with glucal. The radical cyclization of the Ferrier products occurred smoothly to afford cis-fused bicyclic products with the transfer of the chlorine atom at the non-anomeric carbon in the cyclized radical intermediate predominantly from the equatorial direction. The carbohydrate templates controlled the stereochemistry of both Ferrier rearrangement and ATRC steps. The stereostructures of the products were also supported by single crystal X-ray diffraction crystallography. The products possess biologically important structural segments such as a glycosidic linkage, a fused bicyclic acetal unit and a chlorosugar unit which are potential sources for biological studies and further synthetic elaborations. (Figure presented.).
- Ram, Ram N.,Kumar, Neeraj,Gupta, Dharmendra Kumar
-
p. 432 - 442
(2017/02/10)
-
- Site-Selective, Copper-Mediated O-Arylation of Carbohydrate Derivatives
-
Site-selective functionalization of hydroxy groups in sugar derivatives is a major challenge in carbohydrate synthesis. Methods for achieving this goal will provide efficient access to new sugar-derived chemical building blocks and will facilitate the preparation or late-stage modification of complex oligosaccharides for applications in glycobiology research and drug discovery. Here, we describe site-selective, copper-promoted couplings of boronic acids with carbohydrate derivatives. These reactions generate sugar-derived aryl ethers, a structural class that is challenging to generate by other means and has not previously been accessed in a site-selective fashion. Experimental evidence and computational modeling suggest that the formation of a sugar-derived boronic ester intermediate is crucial to the selectivity of these processes, accelerating the arylation of an adjacent hydroxy group. The results demonstrate how the interactions of sugars with boron compounds can be combined with transition metal catalysis to achieve new chemical reactivity.
- Dimakos, Victoria,Garrett, Graham E.,Taylor, Mark S.
-
supporting information
p. 15515 - 15521
(2017/11/06)
-
- Preparation method of glycal
-
The invention belongs to the technical field of chemical engineering and discloses a preparation method of glycal. The method comprises the following steps: (1) adding an organic solvent into a reactor equipped with polyhydroxyaldehyde monosaccharide and a catalyst in an atmosphere of nitrogen, adding a hydroxyl protective agent, carrying out a reflux reaction, and carrying out subsequent processing to obtain a compound a; (2) successively adding ammonium salt and an organic solvent into the compound a under the condition of nitrogen so as to carry out a reaction, and carrying out subsequent processing to obtain a compound b; (3) letting the compound b, substituted hydrazine and a water-removal additive into an organic solvent under the condition of nitrogen so as to carry out a reaction, and carrying out subsequent processing to obtain a compound c; and (4) adding a catalyst and the compound c dissolved in the organic solvent into alkali under the condition of nitrogen, reacting, and carrying out subsequent processing so as to obtain glycal. The preparation method is simple and easy to operate, is low-cost and environment-friendly, and has market advantages. Meanwhile, yield of glycal prepared by the preparation method is good.
- -
-
Paragraph 0044; 0077; 0078
(2017/07/21)
-
- An efficient method for the synthesis of some chlorinated and heteroatom rich triazole-linked β-lactam glycoconjugates
-
The synthetic utility of chlorinated bicyclic C-fused tetrahydrofuro[3,2-c] azetidin-2-ones synthesized in our laboratory by Cu(I)-catalyzed halogen atom transfer radical cyclization (ATRC) has been illustrated through the synthesis of some novel β-lactam glycoconjugates. The chlorine atom of the chloromethyl side chain of the bicyclic C-fused tetrahydrofuro[3,2-c] azetidin-2-ones was subjected to nucleophilic substitution with azide group followed by Cu(I)-catalyzed azide-alkyne click reaction (CuAAC) with propargyl glycosides to generate the desirous β-lactam glycoconjugates. A sequential optimization of the reaction procedure for CuAAC was carried out to obtain an efficient catalyst system to achieve β-lactam glycoconjugates in good yields. The β-lactam glycoconjugates are the compounds of interesting architecture and structurally suitable for bioactivity evaluation. Therefore, these β-lactam glycoconjugates were screened for in vitro antibacterial activity. Additionally, a representative β-lactam glycoconjugate was also tested for biocompatibility and cytotoxic activity against L929 cancer cell lines.
- Dawra, Nisha,Ram, Ram N.
-
supporting information
p. 7982 - 7991
(2016/11/19)
-
- Bisindolyl maleimide derivative and preparation method and application thereof
-
The invention provides a bisindolyl maleimide derivative and a preparation method and application thereof. The bisindolyl maleimide derivative has an excellent alpha-glucosidase inhibition effect and can be used for preventing and treating diabetes.
- -
-
Paragraph 0797
(2017/01/02)
-
- Bisindolylmaleimide derivative, and preparation method and use thereof
-
The invention provides a bisindolylmaleimide derivative, and a preparation method and a use thereof. The bisindolylmaleimide derivative has a good tumor treatment effect, especially has a good treatment effect on some drug-resistant tumors, and can realize accurate treatment of the drug-resistant tumors.
- -
-
Paragraph 0800
(2017/04/03)
-
- TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
-
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
-
supporting information
p. 1758 - 1764
(2016/10/05)
-
- An efficient method for the synthesis of pyranoid glycals
-
A simple and efficient procedure was designed for the preparation of pyranoid glycals. In a novel fashion, a series of protected glycopyranosyl bromides underwent reductive elimination in the presence of zinc dust and ammonium chloride in CH3CN at 30-60 °C. The corresponding glycals were obtained with excellent isolated yields (72-96%) in a short time (20-50 min). Furthermore, the transformation was compatible with different protection patterns and conveniently scalable (86% for 45 g acetobromoglucose) which made it very applicable in organic synthesis.
- Chen, Heshan,Xian, Ting,Zhang, Wan,Si, Wenshuai,Luo, Xiaosheng,Zhang, Bo,Zhang, Meiyu,Wang, Zhongfu,Zhang, Jianbo
-
supporting information
p. 42 - 46
(2016/07/06)
-
- Direct C-H Trifluoromethylation of Glycals by Photoredox Catalysis
-
A mild, efficient, and practical transformation for the direct C-H trifluoromethylation of glycals under visible light has been reported for the first time. This reaction employed fac-Ir3+(ppy)3 as the photocatalyst, Umemoto's reagent as the CF3 source, and a household blue LED or sunlight as the light source. Glycals bearing both electron-withdrawing and -donating protective groups performed this reaction smoothly. This visible light-mediated trifluoromethylation reaction was highlighted by the trifluoromethylation of the biologically important Neu2en moiety.
- Wang, Bang,Xiong, De-Cai,Ye, Xin-Shan
-
supporting information
p. 5698 - 5701
(2015/12/01)
-
- NaBH3CN: A janus substitute for tin-free radical-based reactions
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Beside showing that thermal radical reactions (reduction, Giese reaction) are efficient if bromo-/iodosugars are treated with NaBH3CN and 2,2″-azobisisobutyronitrile, we explored new initiation conditions on the basis of CuI salts (≤0.5 equiv.) supposed to produce radicals from organobromides through a set. This was confirmed, as at about 50 C under an inert atmosphere acetobromoglucose was reduced to the rearranged 2-deoxyglucose and as N-allyl α-bromoamides reacted, depending on the conditions, either by reductive cyclization or atom-transfer radical cyclization. A related cyclization occurred upon using Cu(OAc)2. This and other assays showed the reduction by NaBH3CN of CuII salts, either added or formed in situ. Having both ionic and radical reactivity, NaBH 3CN appears as a Janus reagent that may be useful for tin-free radical chemistry under mild and very simple conditions. Copyright
- Guiard, Julie,Rahali, Yaniss,Praly, Jean-Pierre
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supporting information
p. 4461 - 4466
(2014/08/05)
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- Iterative α-Glycosylation Strategy for 2-Deoxy- and 2,6-Dideoxysugars: Application to the One-Pot Synthesis of Deoxysugar-Containing Oligosaccharides
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This paper describes the development of an iterative and α-selective glycosylation method for 2-deoxyglycosyl and 2,6-dideoxythioglycoside donors based on the DMF modulation concept. We used NMR spectroscopy to probe the 2-deoxyglycosyl imidinium intermediate and elucidated the conditions to decrease the formation of glycal and thus to increase the reaction yields. Further elaboration of the glycosylation method opened the gate for an iterative one-pot synthesis of 2-deoxy- and 2,6-dideoxyglycoside-containing oligosaccharides. An iterative glycosylation method is established for highly reactive 2-deoxyglycosyl donors on the basis of the DMF modulation concept. This method is effective for 2-deoxy- and 2,6-dideoxythioglycosyl donors, and it opens the gate for the one-pot synthesis of deoxysugar-containing oligosaccharides; NIS = N-iodosuccinimide. Tf = trifluoromethylsulfonyl, NAP = 2-naphthylmethyl, STol = p-tolylthio, Bz = benzoyl.
- Chen, Jiun-Han,Ruei, Jyh-Herng,Mong, Kwok-Kong Tony
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p. 1827 - 1831
(2015/10/05)
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- Stereoselective synthesis of α-linked 2-deoxy glycosides enabled by visible-light-mediated reductive deiodination
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2-Deoxy sugars and their derivatives occur abundantly in many pharmaceutically important natural products. However, the construction of specific 2-deoxy-glycosidic bonds remains as a challenge. Herein, we report an efficient way to prepare 2-deoxy-a-glycosides by glycosylation of 2-iodo-glycosyl acetate and subsequent visible-light-mediated tin-free reductive deiodination. We have successfully applied the postglycosylational-deiodination strategy in the synthesis of more than 30 mono-, di-, tri-, tetra- and pentadeoxysaccharides with excellent stereoselectivity and efficiency. This method has also been applied to the synthesis of a 2-deoxy-tetrasac-charide containing four a-linkages.
- Wang, Hao,Tao, Jinyi,Cai, Xinpei,Chen, Wei,Zhao, Yueqi,Xu, Yang,Yao, Wang,Zeng, Jing,Wan, Qian
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supporting information
p. 17319 - 17323
(2015/02/19)
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- Iterative α-glycosylation strategy for 2-deoxy- and 2,6-dideoxysugars: Application to the one-pot synthesis of deoxysugar-containing oligosaccharides
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This paper describes the development of an iterative and α-selective glycosylation method for 2-deoxyglycosyl and 2,6-dideoxythioglycoside donors based on the DMF modulation concept. We used NMR spectroscopy to probe the 2-deoxyglycosyl imidinium intermediate and elucidated the conditions to decrease the formation of glycal and thus to increase the reaction yields. Further elaboration of the glycosylation method opened the gate for an iterative one-pot synthesis of 2-deoxy- and 2,6-dideoxyglycoside-containing oligosaccharides
- Chen, Jiun-Han,Ruei, Jyh-Herng,Mong, Kwok-Kong Tony
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supporting information
p. 1827 - 1831
(2014/04/03)
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- A convenient and efficient synthesis of glycals by zinc nanoparticles
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A simple and efficient method for the synthesis of pyranoid glycals utilizing the reductive elimination of glycopyranosyl bromides by zinc nanoparticles in an acetate buffer is described. A variety of pyranoid glycals derivatives were obtained, especially for the synthesis of 6-deoxy-4,6-O-benzylidene and disaccharide glycals with good yields.
- Xu, Yun,Wang, Wenjun,Cai, Yu,Yang, Xia,Wang, Peng George,Zhao, Wei
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p. 46662 - 46665
(2014/12/10)
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- Phosphodiesters serve as potentially tunable aglycones for fluoro sugar inactivators of retaining β-glycosidases
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2-Deoxy-2-fluoroglycosides bearing dibenzyl phosphate and phosphonate aglycones were synthesised and tested as covalent inactivators of several retaining α- and β-glycosidases. β-d-Gluco-, -manno- and -galacto-configured benzyl-benzylphosphonate derivatives efficiently inactivated β-gluco-, β-manno- and β-galactosidases, while α-gluco- and α-manno-configured phosphate and phosphonate derivatives served instead as slow substrates. This journal is the Partner Organisations 2014.
- Rempel,Withers
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supporting information
p. 2592 - 2595
(2014/04/17)
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- Divergent synthesis of 2-C-branched pyranosides and oxepines from 1,2-gem-dibromocyclopropyl carbohydrates
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The ring opening of 1,2-(gem-dibromo)cyclopropyl carbohydrates by two different modes leads to either 2-C-(bromomethylene)pyranosides (using base) or 2-bromooxepines (using silver salts), as shown previously by us for a D-glucal-derived cyclopropane. The base-promoted ring opening is extended to encompass additional alcohol, thiol and amine nucleophiles, and diastereoisomeric cyclopropane precursors. Cross-coupling of the 2-C-(bromomethylene)pyranosides leads to extended 2-C-branched pyranosides. Silver-promoted ring expansion of the cyclopropyl carbohydrates in the presence of various alcohols is described. Cross-coupling of the resulting benzyl 2-bromooxepines affords 2-C-substituted oxepines.
- Moore, Peter W.,Schuster, Julia K.,Hewitt, Russell J.,Stone, M. Rhia L.,Teesdale-Spittle, Paul H.,Harvey, Joanne E.
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supporting information
p. 7032 - 7043
(2015/02/19)
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- The synthesis of a 2-deoxy-2-acetonyl sugar from its corresponding natural saccharide
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An efficient synthesis of a 2-deoxy-2-acetonyl sugar from its corresponding natural sugar by methallylation of the 2-iodo sugar is reported. The simplified procedure eliminated the need to carry out the reaction under strictly controlled conditions, giving an efficient route for the synthesis of 2-deoxy-2-acetonyl sugar under ordinary laboratory conditions.
- Zhang, Ying,Liu, Yang,Wang, Zhijun,Wang, Zhongfu,Huang, Linjuan
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scheme or table
p. 244 - 246
(2012/09/08)
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- α-Selective organocatalytic synthesis of 2-deoxygalactosides
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Alpha rules: A thiourea acts as an efficient organocatalyst for the glycosylation of protected galactals to form oligosaccharides containing a 2-deoxymonosaccharide moiety (see scheme). The reaction is highly stereoselective for α-linkages and proceeds by way of a syn-addition mechanism. Copyright
- Balmond, Edward I.,Coe, Diane M.,Galan, M. Carmen,McGarrigle, Eoghan M.
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supporting information
p. 9152 - 9155
(2012/10/29)
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- Structurally diverse disaccharide analogs of antifreeze glycoproteins and their ability to inhibit ice recrystallization
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The β-D-galactosyl-(1,3)-α-N-acetyl-D-galactosamine disaccharide is present in antifreeze glycoproteins (AFGPs). Analogs of this disaccharide including the β-linked (1,3)-, (1,4)-, and (1,6)-galactosyl-N-acetyl galactosamine and the β-(1,3)-galactosyl-galactoside were synthesized and evaluated for ice recrystallization inhibition (IRI) activity. The results from this study demonstrate that the b-linked-(1,4) disaccharide exhibits more potent IRI activity than the native b-linked-(1,3) disaccharide. The C2 N-acetyl group of the disaccharide does not affect IRI activity but in monosaccharides, the presence of the C2 N-acetyl group decreases IRI activity. The current study will facilitate the design of potent small-molecule ice recrystallization inhibitors.
- Balcerzak, Anna K.,Ferreira, Sandra S.,Trant, John F.,Ben, Robert N.
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p. 1719 - 1721
(2012/04/04)
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- N-heterocyclic carbene catalyzed C-glycosylation: A concise approach from stetter reaction
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Described herein is the first example of an organocatalytic approach for acylanion addition to the anomeric carbon of 2-nitroglucal using an N-heterocyclic carbene catalyst. Control over the reaction conditions gives β-selective and nitro-eliminated C-glycosides, providing opportunities to produce new classes of C-glycoside.
- Vedachalam, Seenuvasan,Tan, Shi Min,Teo, Hui Ping,Cai, Shuting,Liu, Xue-Wei
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supporting information; experimental part
p. 174 - 177
(2012/02/16)
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- H2SO4-SiO2: Highly efficient and reusable catalyst for per-O-acetylation of carbohydrates under solvent-free conditions
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Sulfuric acid immobilized on silica gel (H2SO 4-SiO2) was used as an efficient promoter for per-O-acetylation of carbohydrates with acetic anhydride under solvent-free conditions. The substrates include not only monosaccharides and disaccharides, but also glycosides. The catalyst is recyclable and stable at room temperature, and the reaction protocol is simple, is cost-effective, and gives good isolated yield with high purity. The large-scale reactions also proceeded conveniently and in high yields. Taylor & Francis Group, LLC.
- Zhang, Jianbo,Zhang, Bo,Zhou, Jiafen,Li, Juan,Shi, Chunjuan,Huang, Ting,Wang, Zhongfu,Tang, Jie
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experimental part
p. 165 - 177
(2012/01/19)
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- Synthesis of nonnatural nucleoside diphosphate sugars
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Recently, we reported an efficient chemical method for the synthesis of a variety of naturally occurring nucleoside diphosphate (NDP) sugars. This method, which is based on the cycloSal approach, can also be used, in principle, for the preparation of rare or even nonnatural NDP sugars. Herein, the syntheses of sulfoquinovose-, glucose-6-sulfate-, L-galactose-, and 2-fluoroglycopyranoside- containing NDP sugars are presented, as well as the synthesis of NDP sugars with non-natural nucleosides. The reactions described gavestereoisomerically defined NDP sugars in high yields and short reaction times.
- Wolf, Saskia,Berrio, Rosmirt Molina,Meier, Chris
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scheme or table
p. 6304 - 6313
(2011/12/16)
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- A rapid synthesis of pyranoid glycals promoted by β-cyclodextrin and ultrasound
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A convenient and environmentally benign procedure for the synthesis of glycals from glycosyl bromides with very low zinc dust loading (1.5 equiv.) is described. The process is activated by β-cyclodextrin and ultrasound. Based on 19 samples, this method has been demonstrated to be highly effective for a broad range of glycosyl bromides, including acid- or base-sensitive and disaccharide glycosyl bromides. A yield of 85%-96% of glycals was obtained. Copyright
- Zhao, Jinzhong,Shao, Huawu,Wu, Xin,Shi, Shaojing
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experimental part
p. 1434 - 1440
(2011/11/05)
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- Combining glycomimetic and multivalent strategies toward designing potent bacterial lectin inhibitors
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As part of ongoing activities toward the design of potent and selective ligands against galactoside-binding proteins from animal, bacterial, and plant lectins, a systematic investigation involving the synthesis and binding evaluations of a series of original β-C-galactopyranoside mimetics is described. The multivalent presentation of partly optimized candidates on various dendritic scaffolds through CuI-catalyzed azide-alkyne cycloaddition (CuAAc) has also been achieved. Biophysical investigations based on isothermal titration calorimetry (ITC) have indicated a dissociation constant in the low micromolar range for the best optimized monovalent conjugate (K d=37 μM). The results thus confirmed that stable C-galactosides could represent efficient synthetic glycomimetics of natural α-linked oligosaccharidic inhibitors of PA-IL lectin (Lec A) from the pathogenic Pseudomonas aeruginosa. Striking enhancements in the avidity of the glycoconjugates were also observed for tri-, hexa-, and nonavalent derivatives, among which the most potent exhibited dissociation constants below 500 nM, corresponding to a 400-fold increase in affinity compared with the β-D-Gal-O-Me used as reference. To deepen our understanding of the binding mode of the best glycomimetics involved in the recognition process, molecular modeling studies, docking calculations, and NMR diffusion measurements have been performed. Although favorable complementary interactions induced by the addition of the hydrophobic aglycon might explain the affinity enhancement, experimental determination of the size and the topology of the multivalent conjugates further supported the formation of aggregative complexes as a major multivalent binding mode. This work represents a systematic and comprehensive study towards a thorough understanding of the protein-carbohydrate interactions involved in Pseudomonas aeruginosa infection, and as such should prove useful for the development of stable and optimized anti-adhesive agents. Copyright
- Chabre, Yoann M.,Giguere, Denis,Blanchard, Bertrand,Rodrigue, Jacques,Rocheleau, Sylvain,Neault, Mathieu,Rauthu, Subhash,Papadopoulos, Alex,Arnold, Alexandre A.,Imberty, Anne,Roy, Rene
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supporting information; experimental part
p. 6545 - 6562
(2011/08/07)
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- Synthesis of Tn/T antigen MUC1 glycopeptide BSA conjugates and their evaluation as vaccines
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The tumor-associated mucin MUC1 over-expressed in most epithelial tumor tissues is considered a promising target for immunotherapy. The extracellular part of MUC1 contains a domain of numerous tandem repeats of the amino acid sequence HGVTSAPDTRPAPGSTAPPA, including five potential O-glycosylation sites. In this study, T9 and S15 have been chosen as the positions of glycosylation. The glycopeptides N-terminally equipped with a triethylene glycol spacer were synthesized by microwave-assisted Fmoc solid-phase peptide synthesis. After detachment from the resin and deprotection, the MUC1 glycopeptides were conjugated to bovine serum albumin (BSA). To evaluate the immunological properties, balb/c mice were immunized with these BSA vaccines. Copyright
- Cai, Hui,Huang, Zhi-Hua,Shi, Lei,Zou, Peng,Zhao, Yu-Fen,Kunz, Horst,Li, Yan-Mei
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scheme or table
p. 3685 - 3689
(2011/09/21)
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- De novo synthesis of a 2-acetamido-4amino-2,4,6-trideoxy-d-galactose (AAT) building block for the preparation of a bacteroides fragilis a1 polysaccharide fragment
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(Figure Presented) Zwitterionic polysaccharides (ZPSs) are potent T-cell activators that naturally occur on the cell surface of bacteria and show potential as immunostimulatory agents. An unusual, yet important component of many ZPSs is 2-acetamido-4-amino-2,4,6-trideoxy-D-galactose (AAT). AAT building block 2 was prepared via a de novo synthesis from N-Cbz-L-threonine 5. Furthermore, building block 2 was used to synthesize disaccharide 15 that constitutes a fragment of zwitterionic polysaccharide A1 (PS A1) found in Bacteroldes fragilis.
- Pragani, Rajan,Stallforth, Pierre,Seeberger, Peter H.
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supporting information; experimental part
p. 1624 - 1627
(2010/06/17)
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- A simple and convenient method for the synthesis of pyranoid glycals
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A simple, mild, and environmentally benign synthesis procedure of pyranoid glycals is described. In a novel fashion, protected glycopyranosyl bromides undergo the reductive elimination in the presence of zinc in phosphate buffer at room temperature. The pyranoid glycals were obtained in good-to-excellent yields (18 examples).
- Zhao, Jinzhong,Wei, Shanqiao,Ma, Xiaofeng,Shao, Huawu
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experimental part
p. 168 - 171
(2011/02/26)
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- Microwave-assisted synthesis of fluorescein-labelled GalNAcα1-O-Ser/ Thr (Tn) glycopeptides as immunological probes
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Fluorescently labelled glycopeptides containing GalNAcα1-O-Ser/Thr residues provide valuable immunological probes for the development of cancer vaccines. The microwave-assisted automated Fmoc solid-phase synthesis of a series of 5(6)-carboxyfluorescein-labelled GalNAcα1-O-Ser/Thr peptides is described. Lys(Dde)-Gly-Wang polystyrene resin was elongated using Fmoc SPPS with incorporation of several GalNAcα1-O-Ser/Thr residues. Deprotection of the Lys(Dde) then allowed attachment of the 5(6)-carboxyfluorescein label. The synthetic methodology described is flexible and suitably robust enabling the incorporation of three contiguous GalNAcα1-O-Ser residues into the peptide chain. Georg Thieme Verlag Stuttgart · New York.
- Lee, Dong Jun,Harris, Paul W.R.,Kowalczyk, Renata,Dunbar, P. Rod,Brimble, Margaret A.
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experimental part
p. 763 - 769
(2010/10/01)
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- Synthesis of glycal-based chiral benzimidazoles by VO(acac) 2-CeCl3 combo catalyst and their self-aggregated nanostructured materials
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(Figure Presented) VO(acac)2-CeCl3 combo catalyst has been developed for chemoselective cyclocondensation cum oxidation under mild reaction conditions toward synthesis of a new class of optically pure compounds, 2-(2′-C-3′,4′,6′-tri-O-benzyl/methyl-glycal)-1H- benzimidazoles. It involves an operationally simple synthetic protocol efficient for the syntheses of a wide range of chiral benzimidazoles in high yields without formation of undesired 1,2-disubstituted and pseudoglycal byproducts. Vanadium(V) is found as active oxidant for the chemical processes which is investigated by UV absorption spectroscopy. Highly ordered one-dimensional low molecular mass organic nanostructured materials are fabricated by nanocrystallization of the chiral nanoscale building blocks. Theoretical calculation by the B3LYP/6-31G** level of theory of the glycal-based chiral benzimidazoles shows out of planar geometry of the 1H-anthra[1,2-d] imidazole-6,11-dione moiety, which is responsible for the strong self-aggregation to generate ultralong nanostructured materials. We have also found nice agreement between the theoretical results with the experimental observation in 2D-NOESY experiments. The photophysical property of the solid nanostructured materials is also reported. 2009 American Chemical Society.
- Maiti, Dilip K.,Halder, Samiran,Pandit, Palash,Chatterjee, Nirbhik,De Joarder, Dripta,Pramanik, Nabyendu,Saima, Yasmin,Patra, Amarendra,Maiti, Prabir K.
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supporting information; experimental part
p. 8086 - 8097
(2010/02/28)
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