ArticleAngewandte Chemie (International ed. in English)2016
An Amidinohydrolase Provides the Missing Link in the Biosynthesis of Amino Marginolactone Antibiotics.
Article in Angewandte Chemie (International ed. in English), 2016. 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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Who cites it
14 citing papers in PubMed.
- Article
- Biosynthesis of macrolactam antibiotics with β-amino acid polyketide starter units.The Journal of antibiotics · 2024Review
- Oxalactam A, a Novel Macrolactam with Potent Anti-Molecules (Basel, Switzerland) · 2022Article
- Structural and functional comparison of Saccharomonospora azurea strains in terms of primycin producing ability.World journal of microbiology & biotechnology · 2020Article
- Identification, cloning and heterologous expression of biosynthetic gene cluster for desertomycin.The Journal of antibiotics · 2020Article
- Nonlinear Biosynthetic Assembly of Alpiniamide by a HybridACS chemical biology · 2020Article
- Article
- Identification of a biosynthetic gene cluster for the polyene macrolactam sceliphrolactam in a Streptomyces strain isolated from mangrove sediment.Scientific reports · 2018Article
- Sulfation and amidinohydrolysis in the biosynthesis of giant linear polyenes.Beilstein journal of organic chemistry · 2017Article
- Polyketide stereocontrol: a study in chemical biology.Beilstein journal of organic chemistry · 2017Review
- A crotonyl-CoA reductase-carboxylase independent pathway for assembly of unusual alkylmalonyl-CoA polyketide synthase extender units.Nature communications · 2016Article
- Flavoenzyme CrmK-mediated substrate recycling in caerulomycin biosynthesis.Chemical science · 2016Article
- An Amidinohydrolase Provides the Missing Link in the Biosynthesis of Amino Marginolactone Antibiotics.Angewandte Chemie (International ed. in English) · 2016Article
- Evidence for an iterative module in chain elongation on the azalomycin polyketide synthase.Beilstein journal of organic chemistry · 2016Article
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Authors and funding
4 authors.
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Abstract
Desertomycin A is an aminopolyol polyketide containing a macrolactone ring. We have proposed that desertomycin A and similar compounds (marginolactones) are formed by polyketide synthases primed not with γ-aminobutanoyl-CoA but with 4-guanidinylbutanoyl-CoA, to avoid facile cyclization of the starter unit. This hypothesis requires that there be a final-stage de-amidination of the corresponding guanidino-substituted natural product, but no enzyme for such a process has been described. We have now identified candidate amidinohydrolase genes within the desertomycin and primycin clusters. Deletion of the putative desertomycin amidinohydrolase gene dstH in Streptomyces macronensis led to the accumulation of desertomycin B, the guanidino form of the antibiotic. Also, purified DstH efficiently catalyzed the in vitro conversion of desertomycin B into the A form. Hence this amidinohydrolase furnishes the missing link in this proposed naturally evolved example of protective-group chemistry.
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