Synthesis of wax esters and related trehalose esters from Mycobacterium avium and other mycobacteria

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  • Salam Taher
  • Juma'a R. Al-Dulayymi
  • H. Griesse Tima
    Scientific Institute of Public Health, Brussels
  • Hanan M. Ali
  • Marta Romano
    Scientific Institute of Public Health, Brussels
  • Mark Baird
The synthesis of mycobacterial mycolic acid related wax esters and of their trehalose di- and mono-esters is described. The trehalose dimycolates (TDMs) synthesised activated bone marrow derived dendritic cells (BMDCs) in vitro more strongly than trehalose dibehenate or the trehalose monomycolates (TMMs). The inflammatory effects were similar to those of TDM from either a synthetic keto- or methoxy-mycolic acid, but somewhat stronger than those of a TDM from an α-mycolic acid. In vivo, the effects of one wax ester TDM were similar to those of the methoxy-MA and α-mycolic acid TDMs and trehalose dibehenate.
Original languageEnglish
Pages (from-to)3863-3876
Number of pages13
JournalTetrahedron
Volume72
Issue number27-28
Early online date6 May 2016
DOIs
Publication statusPublished - 7 Jul 2016
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