Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Streptococcus pneumoniae [ICD11:
XN3PW 
]
Publication DOI: 10.1039/A709293HJournal NLM ID: 7505598Publisher: Chemical Society
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, PO Box 7015, S-750 07 Uppsala, Sweden
The nonasaccharide 1, representing three repeating units of the capsular polysaccharide from Streptococcus pneumoniae 19F, has been synthesized. The synthetic strategy is to first synthesize, by an AB + C route, trisaccharide derivative 14, having O-benzyl groups as persistent, and 1-O-allyl and 4''-O-acetyl groups as temporary, protecting groups. Then, specific replacement of the 1-O-allyl group with an -H-phosphonate monoester gives trisaccharide 17, which is coupled to a spacer. The obtained derivative 18 is then extended from the 4'' end in a stepwise fashion to give compound 20, using trisaccharide 17 and solution-phase H-phosphonate chemistry. Finally, removal of the persistent O-protecting groups gives the nonasaccharide 1.
synthesis, capsular, Streptococcus pneumoniae, capsular polysaccharide
Structure type: oligomer
Location inside paper: p. 1699, nonasaccharide 1
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158557,IEDB_225177,IEDB_885813,IEDB_885823,IEDB_983931,SB_192
Synthetic data: chemical
Comments, role: three repeating units of the capsular polysaccharide, Et3N-salt
NCBI Taxonomy refs (TaxIDs): 1313Reference(s) to other database(s): GlycomeDB:
26111
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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