Glycosylated trehalose. Synthesis of the oligosaccharides of the glycolipid-type antigens from Mycobacterium smegmatis

Zoltán Szurmai, János Kerékgyártó, János Harangi, András Lipták

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The oligosaccharide components, 3-O-Me-β-d-Glcp-(1→3)-β-d-Glcp-(1→4)-β-d-Glcp-(1→6)-α-d-Glcp-(1↔1)-α-d-Glcp (1) and β-d-Glcp-(1→4)-β-d-Glcp-(1→6)-α-d-Glcp-(1↔1)-α-d-Glcp, of the glycolipid-type antigens isolated from M. smegmatis have been synthesised from 2,3,4,2′,3′,4′,6′-hepta-O-acetyl-α,α-trehalose and the appropriate glycosyl bromides under Helferich conditions with Hg(CN)2 as the promoter. Condensation of the trisaccharide glycosyl bromide 27 gave an orthoester derivative (28) which coul dbe rearranged, using HgBr2 or boron trifluoride etherate, into the acetylated derivative (29) of 1. The model compound β-d-Glcp-(1→6)-α-d-Glcp-(1↔1)-α-d-Glcp has also been synthesised.

Original languageEnglish
Pages (from-to)313-325
Number of pages13
JournalCarbohydrate Research
Volume164
Issue numberC
DOIs
Publication statusPublished - Jul 1 1987

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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