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

Disaccharides / chemical synthesis Molecular Conformation Mycobacterium / chemistry Mycolic Acids / chemical synthesis Stereoisomerism
Arabinoglycerol DMAG Dimycoloyl-diarabinoglycerol Mycolic acids

Journal

Chemistry and physics of lipids
ISSN: 1873-2941
Titre abrégé: Chem Phys Lipids
Pays: Ireland
ID NLM: 0067206

Informations de publication

Date de publication:
07 2019
Historique:
received: 08 11 2018
revised: 21 12 2018
accepted: 08 01 2019
pubmed: 15 1 2019
medline: 14 4 2020
entrez: 15 1 2019
Statut: ppublish

Résumé

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.

Identifiants

DOI: 10.1016/j.chemphyslip.2019.01.002 PMID: 30639038
pubmed: 30639038
pii: S0009-3084(18)30208-1
doi: 10.1016/j.chemphyslip.2019.01.002
pii:
doi:

Substances chimiques

Disaccharides 0
Mycolic Acids 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

207-218

Informations de copyright

Copyright © 2019 Elsevier B.V. All rights reserved.

Auteurs

Omar T Ali (OT)

School of Chemistry, Bangor University, Bangor, Gwynedd, LL57 2UW, UK.

Mohsin O Mohammed (MO)

School of Chemistry, Bangor University, Bangor, Gwynedd, LL57 2UW, UK.

Paul J Gates (PJ)

School of Chemistry, Bristol University, Bristol, BS8 1TS, UK.

Mark S Baird (MS)

School of Chemistry, Bangor University, Bangor, Gwynedd, LL57 2UW, UK. Electronic address: chs028@bangor.ac.uk.

Juma'a R Al Dulayymi (JR)

School of Chemistry, Bangor University, Bangor, Gwynedd, LL57 2UW, UK; School of Natural Sciences, Bangor University, Bangor, Gwynedd, LL57 2UW, UK.

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Classifications MeSH

questionsmedicales.fr › Glucides › Sucres › Diholoside › The synthesis of mycobacterial dimycoloyl...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes biochimiques › Conformation moléculaire › The synthesis of mycobacterial dimycoloyl...
questionsmedicales.fr › Bactéries › Bactéries à Gram positif › Bâtonnets à Gram positif › Bâtonnets asporogènes à Gram positif › Bâtonnets asporogènes réguliers à Gram positif › Mycobacteriaceae › Mycobacterium › The synthesis of mycobacterial dimycoloyl...
questionsmedicales.fr › Lipides › Acides gras › Acides mycoliques › The synthesis of mycobacterial dimycoloyl...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes de chimie organique › Isomérie › Stéréoisomérie › The synthesis of mycobacterial dimycoloyl...