The synthesis of single enantiomers of trans-alkene containing mycolic acids and related sugar esters


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Ali H. M. , Koza G., Hameed R. T. , Rowles R., Davies C., Al Dulayymi J. R. , ...More

TETRAHEDRON, vol.72, pp.7143-7158, 2016 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 72
  • Publication Date: 2016
  • Doi Number: 10.1016/j.tet.2016.08.089
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.7143-7158
  • Keywords: Mycolic acid, TDM, TMM, GMM, trans-Alkene, Trehalose monomycolate, Trehalose dimycolate, MYCOBACTERIUM-TUBERCULOSIS, CELL-WALL, CYCLOPROPANE SYNTHETASE, ORGANOCOPPER REAGENTS, HOMOLOGOUS SERIES, WAX ESTERS, BIOSYNTHESIS, SMEGMATIS, MONOMYCOLATE, VIRULENCE

Abstract

Routes to single enantiomers of hydroxy, methoxy and ketomycolic acids containing an alpha-methyl-trans-alkene unit as well as related trehalose, glucose, arabinose and glycerol esters are described. In serodiagnostic assays to detect antibodies to mycobacterial lipids, the trehalose esters give higher responses to the serum of patients with culture positive tuberculosis than to that of culture negative patients. (C) 2016 Elsevier Ltd. All rights reserved.