The synthesis of mycobacterial dimycoloyl diarabinoglycerol based on defined synthetic mycolic acids

Omar T. Ali; Mohsin O. Mohammed; Paul Gates; Mark S. Baird; Juma'a R. Al Dulayymi

doi:10.1016/j.chemphyslip.2019.01.002

The synthesis of mycobacterial dimycoloyl diarabinoglycerol based on defined synthetic mycolic acids

Omar T. Ali, Mohsin O. Mohammed, Paul Gates, Mark S. Baird^*, Juma'a R. Al Dulayymi

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

Complex mixtures of natural dimycoloyl diarabinoglycerols isolated from mycobacteria have been shown to be both potent immune signalling agents and potentially valuable antigens in the serodiagnosis of mycobacterial infections. We now report the highly stereocontrolled synthesis of diacyl L-glycerol-(1′→1)-β-D-arabinofuranosyl-α-D-arabinofuranosides based on simple fatty acids and single defined synthetic mycolic acids. NMR analysis confirmed that the synthetic core was identical to that in natural mixtures.

Original language	English
Pages (from-to)	207-218
Number of pages	12
Journal	Chemistry and Physics of Lipids
Volume	221
Early online date	9 Jan 2019
DOIs	https://doi.org/10.1016/j.chemphyslip.2019.01.002
Publication status	Published - 1 Jul 2019

Keywords

DMAG
Mycolic acids
Arabinoglycerol
Dimycoloyl-diarabinoglycerol

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10.1016/j.chemphyslip.2019.01.002

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@article{370e1c45cc9f451ca120007756822e66,

title = "The synthesis of mycobacterial dimycoloyl diarabinoglycerol based on defined synthetic mycolic acids",

abstract = "Complex mixtures of natural dimycoloyl diarabinoglycerols isolated from mycobacteria have been shown to be both potent immune signalling agents and potentially valuable antigens in the serodiagnosis of mycobacterial infections. We now report the highly stereocontrolled synthesis of diacyl L-glycerol-(1′→1)-β-D-arabinofuranosyl-α-D-arabinofuranosides based on simple fatty acids and single defined synthetic mycolic acids. NMR analysis confirmed that the synthetic core was identical to that in natural mixtures.",

keywords = "DMAG, Mycolic acids, Arabinoglycerol, Dimycoloyl-diarabinoglycerol",

author = "Ali, {Omar T.} and Mohammed, {Mohsin O.} and Paul Gates and Baird, {Mark S.} and {Al Dulayymi}, {Juma'a R.}",

year = "2019",

month = jul,

day = "1",

doi = "10.1016/j.chemphyslip.2019.01.002",

language = "English",

volume = "221",

pages = "207--218",

journal = "Chemistry and Physics of Lipids",

issn = "0009-3084",

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TY - JOUR

T1 - The synthesis of mycobacterial dimycoloyl diarabinoglycerol based on defined synthetic mycolic acids

AU - Ali, Omar T.

AU - Mohammed, Mohsin O.

AU - Gates, Paul

AU - Baird, Mark S.

AU - Al Dulayymi, Juma'a R.

PY - 2019/7/1

Y1 - 2019/7/1

N2 - Complex mixtures of natural dimycoloyl diarabinoglycerols isolated from mycobacteria have been shown to be both potent immune signalling agents and potentially valuable antigens in the serodiagnosis of mycobacterial infections. We now report the highly stereocontrolled synthesis of diacyl L-glycerol-(1′→1)-β-D-arabinofuranosyl-α-D-arabinofuranosides based on simple fatty acids and single defined synthetic mycolic acids. NMR analysis confirmed that the synthetic core was identical to that in natural mixtures.

AB - Complex mixtures of natural dimycoloyl diarabinoglycerols isolated from mycobacteria have been shown to be both potent immune signalling agents and potentially valuable antigens in the serodiagnosis of mycobacterial infections. We now report the highly stereocontrolled synthesis of diacyl L-glycerol-(1′→1)-β-D-arabinofuranosyl-α-D-arabinofuranosides based on simple fatty acids and single defined synthetic mycolic acids. NMR analysis confirmed that the synthetic core was identical to that in natural mixtures.

KW - DMAG

KW - Mycolic acids

KW - Arabinoglycerol

KW - Dimycoloyl-diarabinoglycerol

UR - http://www.scopus.com/inward/record.url?scp=85061135081&partnerID=8YFLogxK

U2 - 10.1016/j.chemphyslip.2019.01.002

DO - 10.1016/j.chemphyslip.2019.01.002

M3 - Article (Academic Journal)

C2 - 30639038

AN - SCOPUS:85061135081

SN - 0009-3084

VL - 221

SP - 207

EP - 218

JO - Chemistry and Physics of Lipids

JF - Chemistry and Physics of Lipids

ER -

The synthesis of mycobacterial dimycoloyl diarabinoglycerol based on defined synthetic mycolic acids

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