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Synthesis and NMR assignment of two repeating units (decasaccharide) of the type III group B Streptococcus capsular polysaccharide and its 13C-labeled and N-propionyl substituted sialic acid analogues

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Subject13C; 13C-NMR; 1H; ACID; analogs & derivatives; assignment; ASSIGNMENTS; bacterial; Bacterial Capsules; Canada; capsular polysaccharide; capsule; Carbohydrate Conformation; Carbohydrate Sequence; chemical; chemical synthesis; chemistry; CONFORMATIONAL; DECASACCHARIDE; donor; epitope; group B Streptococcus; GROUP-B; Magnetic Resonance Spectroscopy; method; Methods; Molecular Sequence Data; N-Acetylneuraminic Acid; NMR; NMR-SPECTRA; oligosaccharide; Oligosaccharides; POLYSACCHARIDE; Polysaccharides; Polysaccharides,Bacterial; PROBES; Propionates; REPEATING UNIT; Repetitive Sequences,Nucleic Acid; SIALIC; SIALIC-ACID; SPECTRA; Streptococcus; Streptococcus agalactiae; Support,U.S.Gov't,P.H.S.; Synthesis; synthetase; TRISACCHARIDE; UNIT
Abstract
For the purpose of carrying out a comprehensive investigation into the nature of the conformational epitope of the type III group B Streptococcus polysaccharide, combined chemical and enzymatic methods were applied to the synthesis of three decasaccharide probes, namely beta-D-Glc-(1-->6)[alpha-NeuR-(2-->3)-beta-D-Gal-(1-->4)] -beta-D-GlcNAc-(1-->3)-beta-D-Gal-(1-->4)-beta-D- Glc-(1-->6)[alpha-NeuR-(2-->3)-beta-D-Gal-(1-->4)]-beta-D-GlcNAc-( 1-->3) -beta-D-Gal-OMe (22 NeuR = NeuAc; 23 NeuR = NeuAc with 8% 13C-labeling; 24 NeuR = NeuPr). The precursor core octasaccharide 21 was chemically synthesized from trisaccharide donor 11 and pentasaccharide acceptor 19 by block condensation. Sialylation of 21 with alpha-(2-->3)-sialyltransferase and CMP-NeuAc afforded 22. In the presence of CMP-sialic acid synthetase and alpha-(2-->3)-sialyltransferase, 21 was sialylated with sialic acid derivatives (8% 13C-labeled, or N-propionyl substituted) to give 23 and 24, respectively. Complete assignments of the 1H and 13C NMR spectra of compounds 21, 22 (23), and 24 are also presented
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  • Carbohydr.Res. 295 (13 December 1996): 209–228.
LanguageEnglish
NRC numberZOU1996
NPARC number9370629
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Record identifier10bbba66-8ee5-4514-825e-e68c53a2225d
Record created2009-07-10
Record modified2020-03-20
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