A novel trisaccharide glycolipid biosurfactant containing trehalose bears ester-linked hexanoate, succinate, and acyloxyacyl moieties: NMR and MS characterization of the underivatized structure

Steven Wynn Esch, Martha D. Morton, Todd D. Williams, Clarence S. Buller

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

A Gram-positive actinomycete growing on n-hexadecane secreted a family of anionic glycolipid surfactant homologs. The major homolog, with a molecular weight of 1210.6347, had the formula C58H98O26. Following mild alkaline saponification, 1H and 13C NMR spectroscopy were used to characterize the non-reducing trisaccharide backbone: β-Glcp-(1→3)-α-Glcp-(1⇆1)-α-Glcp ('laminaratrehalose'). Hexanoate, succinate, 3-hydroxyoctanoate, and 3-hydroxydecanoate were found in 3:1:1:1 molar ratio using GC-EIMS analysis of fatty acid methyl esters (FAME) prepared by transesterification. We found that the β-hydroxy acids bore secondary hexanoate chains in 3-O-ester linkage, giving acyloxyacyl anions of appropriate m/z in FABMS and FABMS/MS spectra. COSY, HETCOR, HMBC, and HMQC NMR experiments established the acylation pattern: succinate at C-2 of the terminal α-glucopyranose ring; hexanoate at C-3'' of the β-glucopyranose ring; 3-hexanoyloxyoctanoate and 3-hexanoyloxydecanoate at the 2'- and 4-positions. In FABMS spectra, the homologs flanked the molecular ion by ±14 and ±28 amu, suggesting heterogeneity in acyl chain length. Copyright (C) 1999 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)112-123
Number of pages12
JournalCarbohydrate Research
Volume319
Issue number1-4
DOIs
StatePublished - Jun 30 1999

Keywords

  • Biosurfactant, anionic
  • Glycolipid, succinylated trehalose
  • Lipooligosaccharide, acyltrehalose
  • Lipopolysaccharide, lipid A
  • Trehalose oligosaccharide, laminaratrehalose
  • Trisaccharide, glucose

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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