Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Streptococcus pneumoniae [ICD11:
XN3PW 
]
NCBI PubMed ID: 11695675Publication DOI: 10.1002/1521-3765(20011015)7:20<4411::aid-chem4411>3.0.co;2-tPublisher: Vch Verlagsgesellschaft
Correspondence: j.f.g.vliegenthart
chem.uu.nl
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry Utrecht University, Utrecht, The Netherlands
The preparation is described of a range of neoglycoproteins containing synthesised fragments of the capsular polysaccharide of Streptococcus pneumoniae type 3, that is β-D-GlcpA-(1→4)-β-D-Glcp-(1→O)-(CH2)3NH2 (1), β-D-Glcp-(1→3)-β-D-GlcpA-(1→4)-β-D-Glcp-(1→O)-(CH2)3NH2 (2), and β-D-GlcpA-(1→4)-β-D-Glcp-(1→3)-β-D-GlcpA-(1→4)-β-D-Glcp-(1→O)-(CH2)3NH2 (3). A blockwise approach was developed for the synthesis of the protected carbohydrate chains, in which the carboxylic groups were introduced prior to deprotection by selective oxidation of HO-6 in the presence of HO-4 by using TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy radical). After deprotection, the 3-aminopropyl spacer of the fragments was elongated with diethyl squarate (3,4-diethoxy-3-cyclobutene-1,2-dione) and the elongated oligosaccharides were conjugated to CRM197 (cross-reacting material of diphtheria toxin), KLH (keyhole limpet hemocyanin) or TT (tetanus toxoid). The resulting neoglycoconjugates varied in oligosaccharide chain length, oligosaccharide loading and protein carrier. These well- defined conjugates are ideal probes for evaluating the influence of the different structural parameters in immunological tests.
Streptococcus pneumoniae, Oligosaccharides, antigens, oxidation, neoglycoconjugate vaccines, Streptococcal vaccines, protecting groups
Structure type: oligomer
Location inside paper: abstract
Trivial name: trisaccharide
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_149553,IEDB_423153,IEDB_983931,SB_192
Biological activity: serological data
Synthetic data: chemical
Comments, role: fragment of capsular polysaccharide
Related record ID(s): 3131, 3339
NCBI Taxonomy refs (TaxIDs): 1313Reference(s) to other database(s): GlycomeDB:
4098
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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