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

Chem Phys Lipids

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

Published: July 2019

AI Article Synopsis

  • - The study focuses on natural compounds called dimycoloyl diarabinoglycerols from mycobacteria, which are important for immune signaling and could help diagnose mycobacterial infections.
  • - Researchers successfully synthesized a specific type of compound, diacyl l-glycerol-(1'→1)-β-d-arabinofuranosyl-α-d-arabinofuranosides, using simple fatty acids and precise synthetic mycolic acids.
  • - Analysis using NMR confirmed that the synthetic compounds matched the structure of those found in natural mixtures, indicating the effectiveness of the synthesis process.

Article 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.

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Source
http://dx.doi.org/10.1016/j.chemphyslip.2019.01.002DOI Listing

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