Mycobacterium alvei (ω-1)-methoxy mycolic acids: Absolute stereochemistry and synthesis. (November 2020)

• Record Type: Journal Article
• Authors: Alhuwaymil, Zamzam S.; Al-araj, Intisar Q.M.; Al Dulayymi, Ahmad R.; Jones, Alison; Gates, Paul J.; Valero-Guillén, Pedro L.; Baird, Mark S.; Al Dulayymi, Juma'a R.
• Is Part Of: Chemistry and physics of lipids. Volume 233(2020)
• Publication Date: 2020-11
• Subjects: Mycobacterium -- Alvei -- Mycolic acid -- (ω-1)-Methoxy -- Synthesis; Lipids -- Periodicals; Lipids -- Periodicals; Lipides -- Périodiques; Lipids; Periodicals; Electronic journals; 547.77
• DOI: 10.1016/j.chemphyslip.2020.104977
• Languages: English
• ISSNs: 0009-3084

Abstract

Highlights: Cells of Mycobacterium alvei are known to contain a unique set of mycolic acids with a (ω-1)-methoxy group; although the various enzymes in the biosynthesis of other types of mycolic acid have been widely studied, the absolute stereochemistry of this substituent, and the biosynthetic route to it are unclear. We now determine the stereochemistry of the (ω-1)-methoxy fragment as R, and describe the synthesis of a major R -(ω-1)-methoxy-mycolic acid and its sugar esters, of its S -epimer, and of two natural M. alvei E, Z -diene mycolic acids. Abstract: Cells of Mycobacterium alvei are known to contain a unique set of mycolic acids with a (ω-1)-methoxy group; although the various enzymes in the biosynthesis of other types of mycolic acid have been widely studied, the biosynthetic route to this substituent is unclear. We now define the stereochemistry of the (ω-1)-methoxy fragment as R, and describe the synthesis of a major R -(ω-1)-methoxy-mycolic acid and its sugar esters, and of two natural M. alvei diene mycolic acids.