Capsular polysaccharide from Streptococcus pneumoniae

The type-specific capsular polysaccharide from Streptococcus pneumoniae type 5 contains 2-acetamido-2,6-dideoxy- -D-x>>/o-hexopyranosyl-4-ulose residues (17). Sugar nucleotides of hexos-4-uloses are important intermediates in the transformation of sugars during the biosynthesis, but this is the only known example of such a sugar as a polysaccharide component. 

K. Leontein, B. Lindberg, J. Lonngren, and D. J. Carlo, Structural studies of the capsular polysaccharide from Streptococcus pneumoniae Type 12 A, Carbohydr. Res., 114 (1983) 257-266. 

Figure 2. Comparison of NMR spectra recorded at 500 MHz for three high molecular weight bacterial polysaccharides. A) Cell wall polysaccharide from Streptococcus mitis J22 at 23° C. B) Capsular polysaccharide of Vibrio cholerae 0139 at 60° C. C) Capsular polysaccharide from Streptococcus pneumoniae type 1 at 50 ° C. ...

Leuconostoc mesenteroides ssp. cremoris PIA2 CPS 6C, the capsular polysaccharide from Streptococcus pneumonia VhC 255... 

C18H32O15 488.442 Repeating unit of the capsular polysaccharide from Streptococcus pneumoniae type 23. 

An example of the use of a post-glycosylation oxidation strategy is presented by the recent synthesis of monomeric and dimeric repeats of the zwitterionic Type 1 capsular polysaccharide from Streptococcus pneumonia (Spl) depicted in... 

Wu X, Cui L, Lipinski T, Bundle DR (2010) Synthesis of monomeric and dimeric repeating units of zwitterionic type 1 capsular polysaccharide from Streptococcus pneumonia. Chem Eur J 16 3476-3488... 

Figure 5.2 Structure of the Disaccharide Repeat Unit of the Type ill Capsular Polysaccharide from Streptococcus pneumoniae...

Apart from L-fucose, 3-amino-3,6-dideoxy-D-galactose169 and the D (Ref. 170) and L (Ref. 171) enantiomers of 2-amino-2,6-dideoxygalac-tose (fucosamine) have been identified in bacterial LPS. 2-Acetamido-4-amino-2,4,6-trideoxy-D-galactopyranose has been isolated1710 from the capsular polysaccharide of Streptococcus pneumoniae. 

Activated leukocytes induce the synthesis and secretion from the liver of an unrelated set of proteins called acute-phase proteins. One such protein, C-reactive protein (CRP) was originally identified as binding to the phosphocholine attachment site of capsular polysaccharide (C-polysaccharide) from Streptococcus pneumoniae. CRP in blood has a half life of less than a day, compared with 4 days for fibrinogen. A continuously elevated... 

Pneumococcal vaccine is a mixture of capsular polysaccharides from 23 of the 83 most prevalent types of Streptococcus pneumoniae seen in the United States. 

The pyruvic acid may also be linked to vicinal positions. When linked to 0-3 and 0-4 of a D-galactopyranosyl residue (40), the dioxolane ring becomes cw-fused. In the limited number of known examples, the absolute configuration at the acetalic carbon atom is (S), as in 40. There are some examples of tra -fused dioxolane rings, and these are more sensitive to hydrolysis with acid than the others. Thus, pyruvic acid is acetalically linked to 0-3 and 0-4 of an a-L-rhamnopyranosyl residue in the Klebsiella type 72 capsular polysaccharide, to 0-2 and 0-3 of an a-D-galactopyranosyl residue in the Streptococcus pneumoniae type 4 capsular polysaccharide, and to 0-2 and 0-3 of a S-D-glucopyranosyluronic acid residue in the Klebsiella K1 capsular polysaccharide. " In the extracellular polysaccharide from... 

There are solitary examples of other alditol phosphates as components of this class of polymers. Arabinitol 1-phosphate is part of the S. pneumoniae type 17F capsular polysaccharide. o-Glucitol 6-phosphate is a component of the group-specific polysaccharide from group B Streptococcus, which has a most unusual, ramified structure. In a polysaccharide from Nocardia... 

Constit. of the capsular antigen of Klebsiella K12, K18, K41 type specific antigen of Streptococcus pneumoniae type 2, type 6A O-antigen of Serratia marces-cens extracellular polysaccharide from Mycobacterium album B-88 in operculinic acid (see 3,12-Dihydroxyhexadecanoic acid) formed from the resin of Ipomoea operculata. 

Reducing disaccharide. Constit. of the repeating unit of the capsular antigen of Klebsiella K32, of the type specific antigen of Streptococcus pneumoniae type 17F, and of the extracellular polysaccharides from various strains of Rhizobium japonicum. Syrup. Md +10.1 (c, 1.3 in MeOH). Mg +4.3 (c, 2 in H2O). 

A series of aldoses has been reductively aminated (NaBH3CN) with octadecylamine to give hydrophobic conjugates as model compounds in the g.c.-m.s. analysis (as the N-acetylated O-trimethylsilyl ether derivatives) of reductivety aminated oligosaccharides from the Streptococcus pneumoniae capsular polysaccharide. Isosorbide dinitrate and its metabolites have been assayed in plasma by g.c. with electron-capture detection. ... 

Many polysaccharides contain branched structures and are chemically modified by the addition of other molecules. Their monomeric or repeat units are often made up of more than one sugar molecule and, consequently, can be quite complex. They form protective capsules of some of the most virulent microorganisms, capsules that, nevertheless, carry information that activate mammalian defenses the immune, interferon, and properdin systems [9, 136]. They are found as key portions of the exoskeletons of insects and arthropods and cell walls of plants and microbes and perform as reserve foodstuffs and important components of intercellular, mucous secretions, synovial and ocular fluids, and blood serum in many organisms. Food Applications compiles recent data on the food applications of marine polysaccharides from such various sources as fishery products, microorganisms, seaweeds, microalgae, and corals [137, 138]. One of the applications of this biopolymer relates to a method for protecting against diseases induced by Streptococcus pneumoniae infections, which comprises mucosal administration of a S. pneumoniae capsular polysaccharide to a patient in need. 

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