ArticleThe Journal of biological chemistry2009
Identification and manipulation of the caprazamycin gene cluster lead to new simplified liponucleoside antibiotics and give insights into the biosynthetic pathway.
Article in The Journal of biological chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 44 papers.
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Who cites it
44 citing papers in PubMed.
- The TetR-like regulator Sco4385 and Crp-like regulator Sco3571 modulate heterologous production of antibiotics inApplied and environmental microbiology · 2025Article
- Review
- Biosynthesis and Genome Mining Potentials of Nucleoside Natural Products.Chembiochem : a European journal of chemical biology · 2023Article
- Origin of the 3-methylglutaryl moiety in caprazamycin biosynthesis.Microbial cell factories · 2022Article
- β-Hydroxylation of α-amino-β-hydroxylbutanoyl-glycyluridine catalyzed by a nonheme hydroxylase ensures the maturation of caprazamycin.Communications chemistry · 2022Article
- Identification and characterization of enzymes involved in the biosynthesis of pyrimidine nucleoside antibiotics.Natural product reports · 2021Review
- Cryptic phosphorylation in nucleoside natural product biosynthesis.Nature chemical biology · 2021Article
- Pyridoxal-5'-phosphate-dependent alkyl transfer in nucleoside antibiotic biosynthesis.Nature chemical biology · 2020Article
- Mechanism of action of nucleoside antibacterial natural product antibiotics.The Journal of antibiotics · 2019Review
- Engineering nucleoside antibiotics toward the development of novel antimicrobial agents.The Journal of antibiotics · 2019Review
- Liposidomycin, the first reported nucleoside antibiotic inhibitor of peptidoglycan biosynthesis translocase I: The discovery of liposidomycin and related compounds with a perspective on their application to new antibiotics.The Journal of antibiotics · 2019Review
- Recent advances in the biosynthesis of nucleoside antibiotics.The Journal of antibiotics · 2019Review
- Production of zosteric acid and other sulfated phenolic biochemicals in microbial cell factories.Nature communications · 2019Article
- Biosynthetic reconstitution of deoxysugar phosphoramidate metalloprotease inhibitors using an N-P-bond-forming kinase.Chemical science · 2019Article
- Enzymatic Synthesis of the Ribosylated Glycyl-Uridine Disaccharide Core of Peptidyl Nucleoside Antibiotics.The Journal of organic chemistry · 2018Article
- Self-Resistance during Muraymycin Biosynthesis: a Complementary Nucleotidyltransferase and Phosphotransferase with Identical Modification Sites and Distinct Temporal Order.Antimicrobial agents and chemotherapy · 2018Article
- Overexpression of a type III PKS gene affording novel violapyrones with enhanced anti-influenza A virus activity.Microbial cell factories · 2018Article
- Identification and Interrogation of the Herbicidin Biosynthetic Gene Cluster: First Insight into the Biosynthesis of a Rare Undecose Nucleoside Antibiotic.Journal of the American Chemical Society · 2017Article
- Heteroatom-Heteroatom Bond Formation in Natural Product Biosynthesis.Chemical reviews · 2017Review
- Nature's combinatorial biosynthesis and recently engineered production of nucleoside antibiotics in Streptomyces.World journal of microbiology & biotechnology · 2017Review
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Caprazamycins are potent anti-mycobacterial liponucleoside antibiotics isolated from Streptomyces sp. MK730-62F2 and belong to the translocase I inhibitor family. Their complex structure is derived from 5'-(beta-O-aminoribosyl)-glycyluridine and comprises a unique N-methyldiazepanone ring. The biosynthetic gene cluster has been identified, cloned, and sequenced, representing the first gene cluster of a translocase I inhibitor. Sequence analysis revealed the presence of 23 open reading frames putatively involved in export, resistance, regulation, and biosynthesis of the caprazamycins. Heterologous expression of the gene cluster in Streptomyces coelicolor M512 led to the production of non-glycosylated bioactive caprazamycin derivatives. A set of gene deletions validated the boundaries of the cluster and inactivation of cpz21 resulted in the accumulation of novel simplified liponucleoside antibiotics that lack the 3-methylglutaryl moiety. Therefore, Cpz21 is assigned to act as an acyltransferase in caprazamycin biosynthesis. In vivo and in silico analysis of the caprazamycin biosynthetic gene cluster allows a first proposal of the biosynthetic pathway and provides insights into the biosynthesis of related uridyl-antibiotics.
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