Synthesis of a tri- and a tetra-saccharide fragment of the capsular polysaccharide of type III group B Streptococcus

  1. Get@NRC: Synthesis of a tri- and a tetra-saccharide fragment of the capsular polysaccharide of type III group B Streptococcus (Opens in a new window)
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Journal titleCarbohydr.Res.
Pages133146; # of pages: 14
Subject1H; analysis; assignment; assignments; bacterial; Canada; capsular polysaccharide; Carbohydrate Sequence; Carbon; Catalysis; chemical synthesis; chemistry; Glycosides; Glycosylation; group B Streptococcus; GROUP-B; Magnetic Resonance Spectroscopy; Molecular Sequence Data; Molecular Structure; oligosaccharide; Oligosaccharides; POLYSACCHARIDE; Polysaccharides; Polysaccharides,Bacterial; RELAXATION; RELAXATION-TIMES; Silver; SPECTRA; SPIN-LATTICE RELAXATION; Streptococcus; Streptococcus agalactiae; Synthesis; TRISACCHARIDE; Trisaccharides
AbstractSyntheses of the propyl glycosides (1-3) of beta-D-Galp-(1----4)-beta-D-GlcpNAc, beta-D-Glcp-(1----6)-[beta-D-Galp-(1----4)]-beta-D-GlcpNAc, and beta-D-Galp-(1----4)-beta-D-Glcp-(1----6)-[beta-D-Galp-(1----)]-beta-D- GlcpNAc, respectively, are reported. Reaction of allyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(4-methoxybenzyl)-beta-D-glucopyranos ide with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide under Hg(CN)2 catalysis, followed by oxidative removal of the 4-methoxybenzyl group, gave allyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-beta-D- galactopyranosyl)-beta-D-glucopyranoside (10) O-deacetylation of which, followed by hydrogenolysis/hydrogenation, gave 1. Reaction of 10 with beta-D-glucopyranose penta-acetate and beta-lactose octa-acetate, under catalysis by trimethylsilyl trifluoromethanesulfonate, and treatment of the products as for 10 gave 2 and 3, respectively. Attempted glycosylation of 10 with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl bromide under catalysis by Hg(CN)2 or silver trifluoromethanesulfonate gave an orthoester. Complete assignments of the 1H- and 13C-n.m.r. spectra of 1-3 are reported together with their carbon spin-lattice relaxation times which indicate that 3 assumes a compact instead of an extended shape
Publication date
AffiliationNRC Institute for Biological Sciences; National Research Council Canada
Peer reviewedNo
NRC numberPOZSGAY1990
NPARC number9388141
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Record identifier50622074-1761-44f2-aa33-ef0faf75e547
Record created2009-07-10
Record modified2016-05-09
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