Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Streptococcus pneumoniae [ICD11:
XN3PW 
]
Publication DOI: 10.1039/A804272AJournal NLM ID: 7505598Publisher: Chemical Society
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Utrecht, The Netherlands
The chemoenzymic synthesis is described of b-D-Galp-(1-4)-b-D-Glcp-(1-6)-[b-D-Galp-(1-4)]-b-DGlcpNAc-(1-O[CH2]3O-4)-b-D-Glcp-(1-OCH2CH=CH2) 32 and b-D-Galp-(1-4)-b-D-GlcpNAc-(1-O[CH2]3O-4)-b-D-Glcp-(1-6)-[b-D-Galp-(1-4)]-b-D-GlcpNAc-(1-O[CH2]3O-4)-b-D-Glcp-(1-OCH2-CH=CH2) 33, representing hexa- and octasaccharide mimics of fragments of the Streptococcus pneumoniae type 14 polysaccharide. In a chemical approach the intermediate linear oligosaccharide mimics 30 and 31 were synthesized, wherein both terminal and non-terminal N-acetyl-b-D-glucosamine residues were not yet galactosylated. The alkyl-bridged derivatives were found to be good acceptor substrates for bovine milk b-1,4-galactosyltransferase. Reaction of the anomeric allyl functions with cysteamine under UV-irradiation gave the corresponding 3-(2-aminoethylthio)propyl glycosides 34 and 35, suitable for further coupling of the oligosaccharide mimics to protein carriers.
synthesis, Streptococcus pneumoniae, capsular polysaccharide
Structure type: polymer chemical repeating unit
Location inside paper: p. 3011
Compound class: CPS, O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_1392542,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_143634,IEDB_146664,IEDB_149138,IEDB_149139,IEDB_149141,IEDB_149142,IEDB_149143,IEDB_149144,IEDB_149145,IEDB_149147,IEDB_149148,IEDB_149149,IEDB_149150,IEDB_149151,IEDB_151531,IEDB_190606,IEDB_983931,SB_145,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_6,SB_7,SB_88
Enzymes that release or process the structure: b-1,4-galactosyltransferase
Synthetic data: chemoenzymatic
Comments, role: published chemical repeating unit frame was shifted for the uniformity of structures in the database
Related record ID(s): 2848, 2849, 5348, 6002, 6406, 7502, 25415, 104240, 110608, 113253, 117208, 130172
NCBI Taxonomy refs (TaxIDs): 1313Reference(s) to other database(s): GTC:G52755VD, GlycomeDB:
2039, CCSD:
11172, CBank-STR:12723
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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