Structural determination of the polar glycoglycerolipids from thermophilic bacteria Meiothermus taiwanensis

Eur J Biochem. 2004 Nov;271(22):4545-51. doi: 10.1111/j.1432-1033.2004.04415.x.

Abstract

The polar glycolipids were isolated from the thermophilic bacteria Meiothermus taiwanensis ATCC BAA-400 by ethanol extraction and purified by Sephadex LH-20 and silica gel column chromatography. The fatty acid composition of O-acyl groups in the glycolipids was obtained by gas chromatography mass spectroscopy analysis on their methyl esters derived from methanolysis and was made mainly of C(15:0) (34.0%) and C(17:0) (42.3%) fatty acids, with the majority as branched fatty acids (over 80%). Removal of O-acyl groups under mild basic conditions provided two glycolipids, which differ only in N-acyl substitution on a hexosamine. Electrospray mass spectroscopy analysis revealed that one has a C(17:0) N-acyl group and the other hydroxy C(17:0) in a ratio of about 1 : 3.5. Furthermore, complete de-lipidation with strong base followed by selective N-acetylation resulted in a homogeneous tetraglycosyl glycerol. The linkages and configurations of the carbohydrate moiety were then elucidated by MS and various NMR analyses. Thus, the major glycolipid from M. taiwanensis ATCC BAA-400 was determined with the following structure: alpha-Galp(1-6)-beta-Galp(1-6)-beta-GalNAcyl(1,2)-alpha-Glc(1,1)-Gro diester, where N-acyl is C(17:0) or hydroxy C(17:0) fatty acid and the glycerol esters were mainly iso- and anteisobranched C(15:0) and C(17:0).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Deinococcus / chemistry*
  • Deinococcus / genetics
  • Gas Chromatography-Mass Spectrometry
  • Glycerides / chemistry*
  • Glycolipids / chemistry*
  • Methyl Ethers / analysis
  • Nuclear Magnetic Resonance, Biomolecular
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Glycerides
  • Glycolipids
  • Methyl Ethers