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

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

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 (...

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Bibliographic Details
Published in:Tetrahedron Vol. 72; no. 27-28; pp. 3863 - 3876
Main Authors: Taher, Salam G., Al Dulayymi, Juma'a R., Tima, H. Giresse, Ali, Hanan M., Romano, Marta, Baird, Mark S.
Format: Journal Article
Language:English
Published: Elsevier Ltd 07-07-2016
Subjects:
Bone marrow
Esters
In vitro testing
Inflammation
Mycobacterium avium
Synthesis
TDM
Tetrahedrons
Time division multiplexing
TMM
Trehalose
Trehalose dimycolate
Trehalose monomycolate
Wax ester
TMM
Trehalose monomycolate
Mycobacterium avium
Inflammation
Trehalose dimycolate
TDM
Wax ester
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Summary: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. [Display omitted]
Bibliography:ObjectType-Article-1
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ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.05.004