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

Zamzam S. Alhuwaymil; Intisar Q.M. Al-araj; Ahmad R. Al Dulayymi; Alison Jones; Paul J. Gates; Pedro L. Valero-Guillén; Mark S. Baird; Juma’a R. Al Dulayymi

doi:10.1016/j.chemphyslip.2020.104977

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

Zamzam S. Alhuwaymil
, Intisar Q.M. Al-araj
, Ahmad R. Al Dulayymi
, Alison Jones
, Paul J. Gates
, Pedro L. Valero-Guillén
, Mark S. Baird
, Juma’a R. Al Dulayymi

University of Bristol
University of Murcia

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

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.

Original language	English
Article number	104977
Number of pages	1
Journal	Chemistry and Physics of Lipids
Volume	233
Early online date	20 Sept 2020
DOIs	https://doi.org/10.1016/j.chemphyslip.2020.104977
Publication status	Published - Nov 2020

Keywords

Mycobacterium
Alvei
Mycolic acid
(ω-1)-Methoxy
Synthesis

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10.1016/j.chemphyslip.2020.104977

https://www.sciencedirect.com/science/article/pii/S0009308420301080

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title = "Mycobacterium alvei (ω-1)-methoxy mycolic acids: Absolute stereochemistry and synthesis",

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.",

keywords = "Mycobacterium, Alvei, Mycolic acid, (ω-1)-Methoxy, Synthesis",

author = "Alhuwaymil, \{Zamzam S.\} and Al-araj, \{Intisar Q.M.\} and Dulayymi, \{Ahmad R. Al\} and Alison Jones and Gates, \{Paul J.\} and Valero-Guill{\'e}n, \{Pedro L.\} and Baird, \{Mark S.\} and Dulayymi, \{Juma{\textquoteright}a R. Al\}",

year = "2020",

month = nov,

doi = "10.1016/j.chemphyslip.2020.104977",

language = "English",

volume = "233",

journal = "Chemistry and Physics of Lipids",

issn = "0009-3084",

publisher = "Elsevier Ireland Ltd",

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TY - JOUR

T1 - Mycobacterium alvei (ω-1)-methoxy mycolic acids: Absolute stereochemistry and synthesis

AU - Alhuwaymil, Zamzam S.

AU - Al-araj, Intisar Q.M.

AU - Dulayymi, Ahmad R. Al

AU - Jones, Alison

AU - Gates, Paul J.

AU - Valero-Guillén, Pedro L.

AU - Baird, Mark S.

AU - Dulayymi, Juma’a R. Al

PY - 2020/11

Y1 - 2020/11

N2 - 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.

AB - 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.

KW - Mycobacterium

KW - Alvei

KW - Mycolic acid

KW - (ω-1)-Methoxy

KW - Synthesis

U2 - 10.1016/j.chemphyslip.2020.104977

DO - 10.1016/j.chemphyslip.2020.104977

M3 - Article

SN - 0009-3084

VL - 233

JO - Chemistry and Physics of Lipids

JF - Chemistry and Physics of Lipids

M1 - 104977

ER -

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

Abstract

Keywords

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