Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Streptococcus [ICD11:
XN3NM 
]
The structure was elucidated in this paperPublication DOI: 10.1016/j.tet.2023.133499Journal NLM ID: 2984170RPublisher: Pergamon Press
Correspondence: A.K. Misra <akmisra69
gmail.com>
Institutions: Bose Institute, Department of Chemical Science, Block EN-80, Sector-V, Salt Lake, Kolkata, 700091, India
A convenient block [3 + 2+1] glycosylation strategy has been developed for the synthesis of sialic acid containing hexasaccharide repeating unit having a 2-aminoethyl linker at the reducing end corresponding to the capsular polysaccharide of Group B Streptococcus type IX strain. A disaccharide thioglycoside has been prepared applying “orthogonal latent-active” glycosylation of a thioglycoside acceptor with a thioglycoside donor. A specially designed sialic acid thioglycoside donor has been used to furnish α-glycosidic linkage. Thioglycosides were used as glycosyl donors throughout the synthetic strategy. A combination of N-iodosuccinimide (NIS) and perchloric acid supported over silica (HClO4–SiO2), a solid acid substitute, was used as a thiophilic promoter for the activation of thioglycosides.
carbohydrates, hexasaccharide, polysaccharide, glycosylation, glycoside
Structure type: oligomer ; 1267.4552 [M+Na]+
C
47H
80N
4O
34Location inside paper: Fig. 1, compound 1, type IX
Aglycon: (1->1) 2-aminoethyl
Compound class: CPS
Contained glycoepitopes: IEDB_130646,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_165,SB_166,SB_170,SB_171,SB_172,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, glycosylation, optical rotation measurement, CC, HR-ESI-MS, 13C DEPT 135
Synthetic data: chemical
Comments, role: hexasaccharide repeating unit of the CPS of Group B Streptococcus (GBS) type IX
NCBI Taxonomy refs (TaxIDs): 1319
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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