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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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FormatTexte, Article
Sujet13C; 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
Résumé
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
Date de publication
Dans
  • Carbohydr.Res. 295 (13 décembre 1996) : 209–228.
Langueanglais
Numéro du CNRCZOU1996
Numéro NPARC9370629
Exporter la noticeExporter en format RIS
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Identificateur de l’enregistrement10bbba66-8ee5-4514-825e-e68c53a2225d
Enregistrement créé2009-07-10
Enregistrement modifié2020-03-20

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