ArticleChembiochem : a European journal of chemical biology2011
Definition of the common and divergent steps in carbapenem β-lactam antibiotic biosynthesis.
Article in Chembiochem : a European journal of chemical biology, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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14 citing papers in PubMed, 36 citations in OpenAlex.
- ThnL, a B12-dependent radicalProceedings of the National Academy of Sciences of the United States of America · 2022Article
- Evolution of Methods for the Study of Cobalamin-Dependent Radical SAM Enzymes.ACS bio & med chem Au · 2022Article
- Asymmetric Alkylation of Ketones Catalyzed by Engineered TrpB.Angewandte Chemie (International ed. in English) · 2021Article
- Concise Synthesis and Antimicrobial Evaluation of the Guanidinium Alkaloid Batzelladine D: Development of a Stereodivergent Strategy.Journal of the American Chemical Society · 2020Article
- Biocatalytic production of bicyclic β-lactams with three contiguous chiral centres using engineered crotonases.Communications chemistry · 2019Article
- 1.8 Å resolution crystal structure of the carbapenem intrinsic resistance protein CarF.Acta crystallographica. Section D, Structural biology · 2017Article
- δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine synthetase (ACVS): discovery and perspectives.Journal of industrial microbiology & biotechnology · 2017Review
- Convergent biosynthetic pathways to β-lactam antibiotics.Current opinion in chemical biology · 2016Review
- Consecutive radical S-adenosylmethionine methylations form the ethyl side chain in thienamycin biosynthesis.Proceedings of the National Academy of Sciences of the United States of America · 2015Article
- Crystal structure of the carbapenem intrinsic resistance protein CarG.Journal of molecular biology · 2014Article
- Identification and characterization of the carbapenem MM 4550 and its gene cluster in Streptomyces argenteolus ATCC 11009.Chembiochem : a European journal of chemical biology · 2014Article
- Mechanistic insights into the bifunctional non-heme iron oxygenase carbapenem synthase by active site saturation mutagenesis.Journal of the American Chemical Society · 2013Article
- Autoproteolytic activation of ThnT results in structural reorganization necessary for substrate binding and catalysis.Journal of molecular biology · 2012Article
- Engineering the synthetic potential of β-lactam synthetase and the importance of catalytic loop dynamics.MedChemComm · 2012Article
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7 authors at 1 institution in 1 country.
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Abstract
Approximately 50 naturally occurring carbapenem β-lactam antibiotics are known. All but one of these have been isolated from Streptomyces species and are disubstituted structural variants of a simple core that is synthesized by Pectobacterium carotovorum (Erwinia carotovora), a phylogenetically distant plant pathogen. While the biosynthesis of the simple carbapenem, (5R)-carbapen-2-em-3-carboxylic acid, is impressively efficient requiring only three enzymes, CarA, CarB and CarC, the formation of thienamycin, one of the former group of metabolites from Streptomyces, is markedly more complex. Despite their phylogenetic separation, bioinformatic analysis of the encoding gene clusters suggests that the two pathways could be related. Here we demonstrate with gene swapping, stereochemical and kinetics experiments that CarB and CarA and their S. cattleya orthologues, ThnE and ThnM, respectively, are functionally and stereochemically equivalent, although their catalytic efficiencies differ. The biosynthetic pathways, therefore, to thienamycin, and likely to the other disubstituted carbapenems, and to the simplest carbapenem, (5R)-carbapen-2-em-3-carboxylic acid, are initiated in the same manner, but share only two common steps before diverging.
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