- Synthesis of the hyper-branched core tetrasaccharide motif of chloroviruses
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Chemical synthesis of complex oligosaccharides, especially those possessing hyper-branched structures with one or multiple 1,2-cisglycosidic bonds, is a challenging task. Complementary reactivity of glycosyl donors and acceptors and proper tuning of the s
- Mishra, Bijoyananda,Manmode, Sujit,Walke, Gulab,Chakraborty, Saptashwa,Neralkar, Mahesh,Hotha, Srinivas
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p. 1315 - 1328
(2021/02/26)
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- Glycoconjugates and use thereof as vaccine against Shigella flexneri serotype 3a and X
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The present invention relates to compounds derived from sugars which reproduce the epitopes of Shigella flexneri serotypes 3a and X and to the use thereof for the preparation of vaccine compositions. More specifically, the subject matter of the present in
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Page/Page column 88-89
(2014/09/03)
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- SYNTHETIC OLIGOSACCHARIDE GROUP A STREPTOCOCCUS
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The present invention provides novel synthetic poly-L-rhamnose oligosaccharides, compositions containing the same, and methods of preventing Group A Streptococcus infections.
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- Novel O-acetylated decasaccharides
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The present invention relates to diversely acetylated decasaccharides of formula (I) representative of two repeating units of Shigella flexneri serotype 2a O-antigen, conjugates and method of preparation thereof. These compounds exhibit antigenic properties and are particularly useful for the diagnosis of Shigella infection. wherein R1 and R2 are as defined in claim 1.
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- Synthesis of branched tri- to pentasaccharides representative of fragments of Shigella flexneri serotypes 3a and/or X O-antigens
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Fragments of the {2)-[α-d-Glcp-(1→3)]-α-l-Rhap-(1→2)-α-l-Rhap-(1→3)-[Ac→2]-α-l-Rhap-(1→3)-β-d-GlcpNAc-(1→}n ((E)ABAcCD)n polymer were synthesized. D(E)A, CD(E)A, AcCD(E)A were obtained according to a linear strategy, whereas BCD(E)A and BAcCD(E)A were derived from the condensation of appropriate BC and D(E)A building blocks. Oligosaccharides were synthesized as their propyl glycoside, relying on (i) the efficient trichloroacetimidate chemistry, (ii) a common EA allyl glycoside, and (iii) a 2-trichloroacetamido-d-glucopyranose precursor to residue D. Final Pd/C-mediated deprotection, run under a high pressure of hydrogen, ensured O-acetyl stability. All targets are parts of the O-antigen of Shigella flexneri 3a, a prevalent serotype. Non-O-acetylated oligosaccharides are shared by the S. flexneri serotype X O-antigen.
- Boutet, Julien,Guerreiro, Catherine,Mulard, Laurence A.
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p. 10558 - 10572
(2008/12/23)
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- Studies on carbohydrates XVIII. Synthesis of tetrasaccharide corresponding to biological repeat units of Serratia marcescens O18 polysaccharide
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The synthesis of a blocked tetrasaccharide portion of the biological repeat unit, [→2)L-Rhapα(1→2)L-Rhapα(1→2)L-Rhapα(1→6)D-GlcNAcpα(1→], of the Serratia marcescens O18 polysaccharide was described. The key intermediate compounds was 3,4-blocked -L-rhamno
- Zhang,Mao,Chen,Cai
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p. 2283 - 2290
(2007/10/02)
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- SYNTHESIS OF NEOGLYCOPROTEINS AS ARTIFICIAL ANTIGENS
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The synthesis of various allyl glycosides of L-rhamnose containing ether and/or ester substituents are reported.Ozonolysis of allyl glycosides followed by reductive amination with ε-amino groups of lysine residues in bovine serum albumin using sodium cyan
- Mahajan, Ritu,Dixit, Sapna,Khare, Naveen K.,Khare, Anakshi
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- Synthesis of Oligosaccharides Corresponding to Biological Repeating Units of Shigella flexneri Variant Y Polysaccharide. Part 1. Overall Strategy, Synthesis of a Key Trisaccharide Intermediate, and Synthesis of a Pentasaccharide
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The overall strategy for the synthesis of penta- up to octa-saccharides, representing the biological repeating unit of the Shigella flexneri serogroup Y lipopolysaccharide, is described.The key intermediate, the common terminal trisaccharide, α-L-Rhap-(1->2)-α-L-Rhap(1->3)-α-L-Rhap, has been synthesised by a series of Koenigs-Knorr reactions.A selectively protected rhamnose intermediate has been developed for the synthesis of this trisaccharide as its allyl glycoside.Allyl α-L-rhamnopyranoside was converted into the corresponding 2-O-benzoyl-4-O-benzyl derivative via a 2,3-orthobenzoate.Koenigs-Knorr reaction between this partially blocked rhamnoside and 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl chloride afforded the blocked disaccharide.Selective transesterification of the 2'-O-acetyl group in the presence of the 2-O-benzoate yielded the disaccharide, selectively deblocked at the C-2' position.Reaction with the same rhamnopyranosyl chloride gave the fully blocked trisaccharide.Deallylation, followed by treatment with NN-dimethyl(chloromethylene)ammonium chloride, then gave the corresponding trisaccharide chloride.In conjunction with the disaccharide methyl 2-O-(2'-acetamido-4',6'-O-benzylidene-2'-deoxy-β-D-glucopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside, the synthesis of the blocked pentasaccharide was accomplished.Transesterification, followed by hydrogenolysis in aqueous acetic acid, afforded the pure pentasaccharide hapten, α-L-Rhap-(1->2)-α-L-Rhap-(1->3)-α-L-Rhap-(1->3)-β-D-GlcpNAc-(1->2)-α-L-Rhap, as its methyl glycoside, for use in binding studies and n.m.r. studies.
- Pinto, B. Mario,Morisette, David G.
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- CHEMICAL SYNTHESIS AND SEROREACTIVITY OF O-(3,6-DI-O-METHYL-β-D-GLUCOPYRANOSYL)-(1-4)-O-(2,3-DI-O-METHYL-α-L-RHAMNOPYRANOSYL)-(1-9)-OXYNONANOYL-BOVINE SERUM ALBUMIN - THE LEPROSY-SPECIFIC, NATURAL DISACCHARIDE-OCTYL-NEOGLYCOPROTEIN
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The outer disaccharide segment, namely, O-(3,6-di-O-methyl-4B-D-glucopyranosyl)-(1-4)-2,3-di-O-methyl-α-L-rhamnopyranose, of the trisaccharide-containing, leprosy-specific, phenolic glycolipid I has been synthesized as the 8-(methoxycarbonyl)octyl glycosi
- Chatterjee, Delphi,Cho, Sang-Nae,Brennan, Patrick J.,Aspinall, Gerald O.
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