Synthesis of structural elements of the capsular polysaccharides of Streptococcus pneumoniae types 6A and 6B

Ted M. Slaghek, Anita H. van Oijen, Augustinus A.M. Maas, Johannis P. Kamerling, Johannes F.G. Vliegenthart*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

23 Citations (Scopus)

Abstract

O-α-d-Glucopyranosyl-(1→3)-α,β-l-rhamnopyranose (15), O-α-d-galactopyranosyl-(1→3)-O-α-d-glucopyranosyl-(1→3)-α,β-l-rhamnopyranose (17), O-α-d-galactopyranosyl-(1→3)-O-α-d-glucopyranosyl-(1→3)-O-α-l-rhamnopyranosyl-(1→3)-d-ribitol (23), and O-α-d-galactopyranosyl-(1→3)-O-α-d-glucopyranosyl-(1→3)-O-α-l-rhamnopyranosyl-(1→4)-d-ribitol (27), which are structural elements of the capsular polysaccharides of Streptococcus pneumoniae types 6A and 6B {[→2)-α-d-Galp-(1→3)-α-d-Glcp-(1→3)-α-l-Rhap-(1→X)-d-Rib-ol-(5-P→]n; 6AXX = 3, 6B X =4}, have been synthesised. Ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-d-glucopyranoside (3) was coupled with benzyl 2,4-di-O-benzyl-α-l-rhamnopyranoside (4), and subsequent deallylation (→14) and debenzylation gave 15. Condensation of 14 with ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-d-galactopyranoside (2) followed by debenzylation gave 17. Acetylation of 17 followed by removal of AcO-1, conversion into the imidate, coupling with 1,2,4,5-tetra-O-benzyl-d-ribitol (11), deacetylation, and debenzylation gave 23. Coupling of the imidate with 1-O-allyloxycarbonyl-2,3,5-tri-O-benzyl-d-ribitol (12) followed by deallyloxycarbonylation, deacetylation, and debenzylation yielded 27.

Original languageEnglish
Pages (from-to)237-248
Number of pages12
JournalCarbohydrate Research
Volume207
Issue number2
DOIs
Publication statusPublished - 25 Oct 1990
Externally publishedYes

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