Structural studies of the capsular polysaccharide from Streptococcus pneumoniae Type 12F

Abstract

The capsular polysaccharide from Streptococcus pneumoniae type 12F is composed of D-glucosyl, D-galactosyl, 2-acetamido-2-deoxy-D-galactosyl, 2-acetamido-2,6-dideoxy-L-galactosyl, and 2-acetamido-2-deoxy-D-mannuronic acid residues in the proportions 2:1:1:1:1. The main structural evidence was adduced from nmr spectroscopy, methylation analysis, and specific degradations whereby it could be concluded that the polysaccharide is composed of hexasaccharide repeating-units having the structure:[Formula: see text]

Immunogenicity and immunochemistry ofStreptococcus pneumoniae capsular polysaccharides

“…The conjugate elicited antibodies in young mice and had TD properties as it gave booster responses (Fattom et al 1988). $12A has significant structural features in common (Table 2: 20, 21) (Leontein et al 1981(Leontein et al , 1983, which accounts for its serological reactions (Lund 1970).…”

Structures and biological activities of cladolosides C3, E1, E2, F1, F2, G, H1 and H2, eight triterpene glycosides from the sea cucumber Cladolabes schmeltzii with one known and four new carbohydrate chains

“…The HR ESI MS (positive ion mode) of 1 exhibited a pseudomolecular ion peak [MþNa] Absolute D-configurations of the sugars in the glycoside 1 and all the other glycosides were found using acid hydrolysis of the total glycosidic fraction from C. schmeltzii with TFA followed by alcoholysis by R-(À)-2-octanol with subsequent acetylation and GLC analysis using authentic 3-O-methyl-D-glucose, D-glucose, D-quinovose and D-xylose samples for comparison. 6 All these data indicated that cladoloside C 3 Analysis of the 1 H and 13 C NMR spectra (C 5 D 5 N) (Table 2SD) of the aglycone parts of cladolosides E 1 (2), F 1 (4) and H 1 (7) showed their identity to each other and suggested the presence of the same holostane-type nucleus as in cladoloside C 3 (1). There were differences in the side chains signals.…”

“…Glycosides from this species, belonging to the group of cladolosides A contain tetrasaccharide carbohydrate chains differing by the third monosaccharide unit and aglycone structures, 1 the group of cladolosides B is characterized by the identical pentasaccharide carbohydrate moieties with the glucose residue as the fifth sugar unit; the glycosides belonging to the group of cladolosides C have hexasaccharide carbohydrate chains with glucose and 3-O-methylglucose units as the fifth and the sixth sugar units, correspondingly; and cladoloside D, the only glycoside with new hexasaccharide carbohydrate chain, is characterized by the presence of xylose and glucose as the fifth and the terminal sugar units, correspondingly. 2 In a continuation of these investigations, herein we describe the isolation and structural elucidation of new triterpene pentaosides, cladolosides E 1 (2), E 2 (3), F 1 (4) and F 2 (5), and new hexaosides, cladolosides C 3 (1), G (6), H 1 (7) and H 2 (8) with diverse structures of carbohydrate moieties. Structures of these glycosides were elucidated by extensive analysis of the 1 H and 13 C NMR spectra and 2D NMR ( 1 He 1 H COSY, 1D TOCSY, HMBC, HSQC, ROESY) and confirmed by HR ESI mass spectrometry.…”

Carbohydrate Analysis of Bacterial Polysaccharides by High-pH Anion-Exchange Chromatography and Online Polarimetric Determination of Absolute Configuration

“…The OR response for fucosamine, which is substantial as could be expected from its specific rotation (Table 1), clearly points out the difference in optical rotation between Spt12F (-) and BO6 (ϩ). The other neutral constituent monosaccharides of Spt12F are, in order of (24). Noteworthy in the case of BO6 are the largely overlapping peaks for quinovosamine and rhamnosamine (Fig.…”

“…Each PS was analyzed multiple times and the results are summarized in Table 2. The CPS of S. pneumoniae type 12F (Spt12F) among other sugars contains L-fucosamine (24), while the CPS of V. vulnificus strain BO62316 (BO6) has one residue of D-fucosamine in its repeating unit (22,34). In both CPSs, the fucosamine is found as an N-acetyl derivative, but that group is lost upon acid hydrolysis.…”