Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: pneumonia [ICD11:
CA40 
];
bacteremia [ICD11:
MA15.0 ];
meningitis [ICD11:
1D01 ];
infection due to Streptococcus pneumoniae [ICD11:
XN3PW ]
Publication DOI: 10.3762/bjoc.14.95Journal NLM ID: 101250746Publisher: Beilstein-Institut
Correspondence: ghoshrina
yahoo.com
Institutions: Department of Chemistry, Jadavpur University, 188, Raja S. C. Mullick Rd., Kolkata 700032, India, Department of Chemical Sciences, Indian Institute of Science Education and Research, Kolkata, Mohanpur, 741246, West Bengal, India
Streptococcus pneumonia (SPn) is a Gram-positive bacterium which causes life threatening diseases. The bacteria protect themselves against non-specific host defence by an external polysaccharide (PS) capsule which bears a repeating unit, α-D-Galp(1→3)-α-D-Glcp(1→3)-α-L-Rhap(1→3)-D-Rib (SPn 6A). A closer look at the structure reveals the presence of α-linked galactose and glucose residues. The synthesis of these 1,2-cis glycosidic linkages are considered challenging particularly in the context of a one-pot oligosaccharide synthesis. We have synthesized the aforesaid tetrasaccharide (SPn 6A) based on both stepwise and sequential one-pot glycosylation reactions using easily accessible common building blocks; eventually similar overall yields were obtained in both cases.
carbohydrates, Oligosaccharides, glycosylation, total synthesis, stereoselectivity
Structure type: polymer chemical repeating unit
Location inside paper: p.1096, fig.1, SPn6C
Compound class: CPS, K-antigen
Contained glycoepitopes: IEDB_114703,IEDB_136105,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153751,IEDB_153754,IEDB_158539,IEDB_225177,IEDB_591403,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, chemical synthesis, chemical methods, glycosylation
Related record ID(s): 12885, 13115
NCBI Taxonomy refs (TaxIDs): 1313Reference(s) to other database(s): GTC:G06223SK, GlycomeDB:
34761
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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