ArticleJournal of the American Chemical Society2013
Non-ribosomal propeptide precursor in nocardicin A biosynthesis predicted from adenylation domain specificity dependent on the MbtH family protein NocI.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 60 citations in OpenAlex.
- Heterologous expression of NRPS and PKS pathways in Escherichia coli: from bottlenecks to biosynthetic platforms.Essays in biochemistry · 2026Review
- Colorimetric Determination of Adenylation Domain Activity in Nonribosomal Peptide Synthetases by Using Chrome Azurol S.Chembiochem : a European journal of chemical biology · 2023Article
- Structural Studies of Modular Nonribosomal Peptide Synthetases.Methods in molecular biology (Clifton, N.J.) · 2023Article
- Improved l-phenylglycine synthesis by introducing an engineered cofactor self-sufficient system.Synthetic and systems biotechnology · 2022Article
- Acyl Donor Stringency and Dehydroaminoacyl Intermediates in β-Lactam Formation by a Non-ribosomal Peptide Synthetase.ACS chemical biology · 2021Article
- Label-free proteomic dissection on dptP-deletion mutant uncovers dptP involvement in strain growth and daptomycin tolerance of Streptomyces roseosporus.Microbial biotechnology · 2021Article
- Role of Two Exceptional trans Adenylation Domains and MbtH-like Proteins in the Biosynthesis of the Nonribosomal Peptide WS9324A from Streptomyces calvus ATCC 13382.Chembiochem : a European journal of chemical biology · 2020Article
- Functional Cross-Talk of MbtH-Like Proteins During Thaxtomin Biosynthesis in the Potato Common Scab PathogenFrontiers in microbiology · 2020Article
- Structure of a bound peptide phosphonate reveals the mechanism of nocardicin bifunctional thioesterase epimerase-hydrolase half-reactions.Nature communications · 2019Article
- The structural basis of N-acyl-α-amino-β-lactone formation catalyzed by a nonribosomal peptide synthetase.Nature communications · 2019Article
- Using MbtH-Like Proteins to Alter the Substrate Profile of a Nonribosomal Peptide Adenylation Enzyme.Chembiochem : a European journal of chemical biology · 2018Article
- Roles of 2-oxoglutarate oxygenases and isopenicillin N synthase in β-lactam biosynthesis.Natural product reports · 2018Review
- Heteroatom-Heteroatom Bond Formation in Natural Product Biosynthesis.Chemical reviews · 2017Review
- Identification and Characterization of the Sulfazecin Monobactam Biosynthetic Gene Cluster.Cell chemical biology · 2017Article
- Convergent biosynthetic pathways to β-lactam antibiotics.Current opinion in chemical biology · 2016Review
- An Activator of an Adenylation Domain Revealed by Activity but Not Sequence Homology.Chembiochem : a European journal of chemical biology · 2016Article
- Linking Biosynthetic Gene Clusters to their Metabolites via Pathway- Targeted Molecular Networking.Current topics in medicinal chemistry · 2016Review
- Direct Capture Technologies for Genomics-Guided Discovery of Natural Products.Current topics in medicinal chemistry · 2016Review
- Directed evolution of the tryptophan synthase β-subunit for stand-alone function recapitulates allosteric activation.Proceedings of the National Academy of Sciences of the United States of America · 2015Article
- β-Lactam formation by a non-ribosomal peptide synthetase during antibiotic biosynthesis.Nature · 2015Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Nocardicin A is a monocyclic β-lactam isolated from the actinomycete Nocardia uniformis that shows moderate antibiotic activity against a broad spectrum of gram-negative bacteria. The monobactams are of renewed interest due to emerging gram-negative strains resistant to clinically available penicillins and cephalosporins. Like isopenicillin N, nocardicin A has a tripeptide core of non-ribosomal origin. Paradoxically, the nocardicin A gene cluster encodes two non-ribosomal peptide synthetases (NRPSs), NocA and NocB, predicted to encode five modules pointing to a pentapeptide precursor in nocardicin A biosynthesis, unless module skipping or other nonlinear reactions are occurring. Previous radiochemical incorporation experiments and bioinformatic analyses predict the incorporation of p-hydroxy-L-phenylglycine (L-pHPG) into positions 1, 3, and 5 and L-serine into position 4. No prediction could be made for position 2. Multidomain constructs of each module were heterologous expressed in Escherichia coli for determination of the adenylation domain (A-domain) substrate specificity using the ATP/PPi exchange assay. Three of the five A-domains, from modules 1, 2, and 4, required the addition of stoichiometric amounts of MbtH family protein NocI to detect exchange activity. On the basis of these analyses, the predicted product of the NocA and NocB NRPSs is L-pHPG-L-Arg-D-pHPG-L-Ser-L-pHPG, a pentapeptide. Despite being flanked by non-proteinogenic amino acids, proteolysis of this pentapeptide by trypsin yields two fragments from cleavage at the C terminus of the L-Arg residue. Thus, a proteolytic step is likely involved in the biosynthesis of nocardicin A, a rare but precedented editing event in the formation of non-ribosomal natural products that is supported by the identification of trypsin-encoding genes in N. uniformis.
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