ArticleProceedings of the National Academy of Sciences of the United States of America1996
A common mechanism for the biosynthesis of methoxy and cyclopropyl mycolic acids in Mycobacterium tuberculosis.
Article in Proceedings of the National Academy of Sciences of the United States of America, 1996. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
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36 citing papers in PubMed, 127 citations in OpenAlex.
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- Structure and dynamics of the essential endogenous mycobacterial polyketide synthase Pks13.Nature structural & molecular biology · 2023Article
- The pathogenic mechanism of Mycobacterium tuberculosis: implication for new drug development.Molecular biomedicine · 2022Review
- Profiling Pretomanid as a Therapeutic Option for TB Infection: Evidence to Date.Drug design, development and therapy · 2021Review
- Depletion of the DarG antitoxin in Mycobacterium tuberculosis triggers the DNA-damage response and leads to cell death.Molecular microbiology · 2020Article
- Impact of the epoxide hydrolase EphD on the metabolism of mycolic acids in mycobacteria.The Journal of biological chemistry · 2018Article
- CD1b-restricted GEM T cell responses are modulated byProceedings of the National Academy of Sciences of the United States of America · 2017Article
- Biosynthesis: SAM cycles up for colibactin.Nature chemical biology · 2017Article
- Expression of Genes for a Flavin Adenine Dinucleotide-Binding Oxidoreductase and a Methyltransferase fromFrontiers in microbiology · 2017Article
- Determining the mode of action of anti-mycobacterial C17 diyne natural products using expression profiling: evidence for fatty acid biosynthesis inhibition.BMC genomics · 2016Article
- Genomic potential for arsenic efflux and methylation varies among global Prochlorococcus populations.The ISME journal · 2016Article
- New approaches to target the mycolic acid biosynthesis pathway for the development of tuberculosis therapeutics.Current pharmaceutical design · 2014Review
- Rv0132c of Mycobacterium tuberculosis encodes a coenzyme F420-dependent hydroxymycolic acid dehydrogenase.PloS one · 2013Article
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- S-Adenosylmethionine-dependent alkylation reactions: when are radical reactions used?Bioorganic chemistry · 2011Review
- Characterization and analysis of the cotton cyclopropane fatty acid synthase family and their contribution to cyclopropane fatty acid synthesis.BMC plant biology · 2011Article
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2 authors at 2 institutions in 1 country.
Funding
Abstract
Mycobacterium tuberculosis produces three classes of mycolic acids that differ primarily in the presence and nature of oxygen-containing substituents in the distal portion of the meromycolate branch. The methoxymycolate series has a methoxy group adjacent to a methyl branch, in addition to a cyclopropane in the proximal position. Using the gene for the enzyme that introduces the distal cyclopropane (cma1) as a probe, we have cloned and sequenced a cluster of genes coding for four highly homologous methyl transferases (mma1-4). When introduced into Mycobacterium smegmatis, this gene cluster conferred the ability to synthesize methoxymycolates. By determining the structure of the mycolic acids produced following expression of each of these genes individually and in combination, we have elucidated the biosynthetic steps responsible for the production of the major series of methoxymycolates. The mma4 gene product (MMAS-4) catalyzes an unusual S-adenosyl-L-methionine-dependent transformation of the distal cis-olefin into a secondary alcohol with an adjacent methyl branch. MMAS-3 O-methylates this secondary alcohol to form the corresponding methyl ether, and MMAS-2 introduces a cis-cyclopropane in the proximal position of the methoxy series. The similarity of these reactions and the enzymes that catalyze them suggests that some of the structural diversity of mycolic acids results from different chemical fates of a common cationic intermediate, which in turn results from methyl group addition to an olefinic mycolate precursor.
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