Preparation of the pentasaccharide hapten of the GPL of Mycobacterium avium serovar 19 by achieving the glycosylation of a tertiary hydroxyl group

Anikó Fekete, Katalin Gyergyói, K. Kövér, István Bajza, A. Lipták

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The chemical synthesis of the glycopeptidolipid-type pentasaccharide hapten of Mycobacterium avium serovar 19 with a trifluoroacetamido spacer at the reducing end is described. The spacer-armed pentasaccharide 31, when conjugated to an immunogenic protein, can be applied to the serodiagnosis of mycobacterial infections. The questionable structure of the penultimate monosaccharide unit was clarified as 6-deoxy-3-C-methyl-2,4-di-O-methyl-l-mannopyranose. The occurrence of the 6-deoxy-3-C-methyl-2,4-di-O-methyl-l-talopyranose could be excluded by the presence of the large H-1′-H-2′ coupling constant, which proves the 4C1 (l) conformation as the favoured one.

Original languageEnglish
Pages (from-to)1312-1321
Number of pages10
JournalCarbohydrate Research
Volume341
Issue number10
DOIs
Publication statusPublished - Jul 24 2006

Fingerprint

Glycosylation
Mycobacterium avium
Monosaccharides
Haptens
Serologic Tests
Mannose
Hydroxyl Radical
Conformations
Infection
Proteins
Serogroup

Keywords

  • Hapten
  • Mycobacteria
  • Oligosaccharides

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Preparation of the pentasaccharide hapten of the GPL of Mycobacterium avium serovar 19 by achieving the glycosylation of a tertiary hydroxyl group. / Fekete, Anikó; Gyergyói, Katalin; Kövér, K.; Bajza, István; Lipták, A.

In: Carbohydrate Research, Vol. 341, No. 10, 24.07.2006, p. 1312-1321.

Research output: Contribution to journalArticle

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