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- Title
Synthesis of building blocks for an iterative approach towards oligomers of the Streptococcus pneumoniae type 1 zwitterionic capsular polysaccharide repeating unit.
- Authors
Ní Cheallaigh, Aisling; Oscarson, Stefan
- Abstract
Zwitterionic capsular polysaccharide extracts, ∼8 kDa in mass, from Streptococcus pneumoniae type 1 ( Spt1) have shown unique T-cell activating properties. Oligomers of the trisaccharide repeating unit of the Spt1 capsular polysaccharide [→3)-4-NH2-α- d-Qui pNAc-(1→4)-α- d-Gal pA-(1→3)-α- d-Gal pA-(1-] n of defined length are needed to further investigate this response. An approach towards iteratively extendable trisaccharide building blocks of the zwitterionic capsular polysaccharides of Spt1 is described. Key elements include the comparison of pre-glycosylation oxidation and post-glycosylation oxidation approaches using thioglycoside donors to the target trisaccharide, the optimisation of the post-glycosylation oxidation approach, and the conversion of the trisaccharide to building blocks tailored for iterative glycosylation. The construction and evaluation of stereotunable 2- N- 3- O-oxazolidinone donors for the common bacterial 2-acetamido-4-amino-2,4,6-trideoxy-α- d-galactopyranoside motif is also described, as is a key intermediate for their efficient synthesis.
- Subjects
STREPTOCOCCUS pneumoniae; OLIGOMERIZATION; POLYSACCHARIDES; T cells; GLYCOSYLATION
- Publication
Canadian Journal of Chemistry, 2016, Vol 94, Issue 11, p940
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/cjc-2016-0006