Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Host organism: Homo sapiens
Associated disease: bacterial septicemia [ICD11:
MA15.Y 
];
meningitis [ICD11:
1D01 ];
infection due to Streptococcus agalactiae [ICD11:
XN0KC ]
NCBI PubMed ID: 25674920Publication DOI: 10.1021/ol5036563Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: zwguo
chem.wayne.edu
Institutions: Department of Chemistry, Wayne State University , 5101 Cass Avenue, Detroit, Michigan 48202, United States
The structure of the capsular polysaccharide (CPS) of serotype Ia group B Streptococcus (GBS) has been characterized for years, but its repeating unit, which is a challenging pentasaccharide with a branch and a difficult α-sialic acid linkage, has not been synthesized yet. In this report, an effective synthesis was developed for the serotype Ia GBS CPS repeating unit, which had a reactive functionality linked to its main-chain reducing end to enable further elaboration, such as coupling with carrier proteins. The target molecule was accomplished by a convergent [2 + 3] glycosylation strategy employing a sialo-disaccharide as donor and a branched trisaccharide as acceptor. The strategy was designed to suit the synthesis of oligomers of the repeating unit.
capsular polysaccharide, glycosylation, Streptococcus agalactiae
Structure type: polymer chemical repeating unit
Location inside paper: p.1102, fig.1
Trivial name: PS-Ia
Compound class: CPS, EPS
Contained glycoepitopes: IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141588,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149144,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_145,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_6,SB_68,SB_7,SB_84,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, MALDI-TOF MS, NMR-1D, glycosylation
Comments, role: published polymerization frame was shifted for conformity with other records.
Related record ID(s): 30818
NCBI Taxonomy refs (TaxIDs): 355315Reference(s) to other database(s): GTC:G97670WK, GlycomeDB:
15760
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There is only one chemically distinct structure:
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