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

Hanan M. Ali; Gani Koza; Rwoa'a T. Hameed; Richard Rowles; Carys Davies; Juma'a R. Al Dulayymi; Christopher D. Gwenin; Mark S. Baird

doi:10.1016/j.tet.2016.08.089

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

Hanan M. Ali
, Gani Koza
, Rwoa'a T. Hameed
, Richard Rowles
, Carys Davies
, Juma'a R. Al Dulayymi
, Christopher D. Gwenin
, Mark S. Baird^*

^*Corresponding author for this work

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

10 Citations (Scopus)

Abstract

Routes to single enantiomers of hydroxy, methoxy and ketomycolic acids containing an α-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.

Original language	English
Pages (from-to)	7143-7158
Number of pages	16
Journal	Tetrahedron
Volume	72
Issue number	45
Early online date	14 Sept 2016
DOIs	https://doi.org/10.1016/j.tet.2016.08.089
Publication status	Published - 10 Nov 2016
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Mycolic acid
TDM
TMM
GMM
Trans-alkene
Trehalose monomycolate
Trehalose dimycolate

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10.1016/j.tet.2016.08.089

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title = "The synthesis of single enantiomers of trans-alkene containing mycolic acids and related sugar esters",

abstract = "Routes to single enantiomers of hydroxy, methoxy and ketomycolic acids containing an α-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.",

author = "Ali, \{Hanan M.\} and Gani Koza and Hameed, \{Rwoa'a T.\} and Richard Rowles and Carys Davies and \{Al Dulayymi\}, \{Juma'a R.\} and Gwenin, \{Christopher D.\} and Baird, \{Mark S.\}",

note = "Funding Information: HMA and RTH wish to thank the Government of Iraq for the award of PhD studentships. CR thanks the Welsh Government for support under the A4B programme. We wish to thank Dr. Paul Gates of Bristol University for carrying out accurate mass MALDI determinations, and Dr. A Ramsay and the Special Programme for Research and Training in Tropical Diseases at the WHO for access to sera from the TDR TB Specimen Bank. Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2016",

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day = "10",

doi = "10.1016/j.tet.2016.08.089",

language = "English",

volume = "72",

pages = "7143--7158",

journal = "Tetrahedron",

issn = "0040-4020",

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number = "45",

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T1 - The synthesis of single enantiomers of trans-alkene containing mycolic acids and related sugar esters

AU - Ali, Hanan M.

AU - Koza, Gani

AU - Hameed, Rwoa'a T.

AU - Rowles, Richard

AU - Davies, Carys

AU - Al Dulayymi, Juma'a R.

AU - Gwenin, Christopher D.

AU - Baird, Mark S.

N1 - Funding Information: HMA and RTH wish to thank the Government of Iraq for the award of PhD studentships. CR thanks the Welsh Government for support under the A4B programme. We wish to thank Dr. Paul Gates of Bristol University for carrying out accurate mass MALDI determinations, and Dr. A Ramsay and the Special Programme for Research and Training in Tropical Diseases at the WHO for access to sera from the TDR TB Specimen Bank. Publisher Copyright: © 2016 Elsevier Ltd

PY - 2016/11/10

Y1 - 2016/11/10

N2 - Routes to single enantiomers of hydroxy, methoxy and ketomycolic acids containing an α-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.

AB - Routes to single enantiomers of hydroxy, methoxy and ketomycolic acids containing an α-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.

U2 - 10.1016/j.tet.2016.08.089

DO - 10.1016/j.tet.2016.08.089

M3 - Article

AN - SCOPUS:84991716217

SN - 0040-4020

VL - 72

SP - 7143

EP - 7158

JO - Tetrahedron

JF - Tetrahedron

IS - 45

ER -

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

Abstract

UN SDGs

Keywords

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