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

Salam Taher; Juma'a R. Al-Dulayymi; H. Griesse Tima; Hanan M. Ali; Marta Romano; Mark Baird

doi:10.1016/j.tet.2016.05.004

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

Salam Taher, Juma'a R. Al-Dulayymi, H. Griesse Tima, Hanan M. Ali, Marta Romano, Mark Baird

Scientific Institute of Public Health, Brussels

Research output: Contribution to journal › Article › peer-review

Abstract

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 language	English
Pages (from-to)	3863-3876
Number of pages	13
Journal	Tetrahedron
Volume	72
Issue number	27-28
Early online date	6 May 2016
DOIs	https://doi.org/10.1016/j.tet.2016.05.004
Publication status	Published - 7 Jul 2016

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title = "Synthesis of wax esters and related trehalose esters from Mycobacterium avium and other mycobacteria",

abstract = "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.",

author = "Salam Taher and Al-Dulayymi, \{Juma'a R.\} and Tima, \{H. Griesse\} and Ali, \{Hanan M.\} and Marta Romano and Mark Baird",

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T1 - Synthesis of wax esters and related trehalose esters from Mycobacterium avium and other mycobacteria

AU - Taher, Salam

AU - Al-Dulayymi, Juma'a R.

AU - Tima, H. Griesse

AU - Ali, Hanan M.

AU - Romano, Marta

AU - Baird, Mark

PY - 2016/7/7

Y1 - 2016/7/7

N2 - 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.

AB - 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.

U2 - 10.1016/j.tet.2016.05.004

DO - 10.1016/j.tet.2016.05.004

M3 - Article

SN - 0040-4020

VL - 72

SP - 3863

EP - 3876

JO - Tetrahedron

JF - Tetrahedron

IS - 27-28

ER -

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

Abstract

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