ArticleNature chemical biology2011
Reveromycin A biosynthesis uses RevG and RevJ for stereospecific spiroacetal formation.
Article in Nature chemical biology, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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Who cites it
31 citing papers in PubMed, 84 citations in OpenAlex.
- Biosynthesis of reveromycin derivatives by altering the regioselectivity of cytochrome P450revI.Chemical science · 2025Article
- An enzymatic dual-oxa Diels-Alder reaction constructs the oxygen-bridged tricyclic acetal unit of (-)-anthrabenzoxocinone.Nature chemistry · 2025Article
- Chemical biology research in RIKEN NPDepo aimed at agricultural applications.Proceedings of the Japan Academy. Series B, Physical and biological sciences · 2025Review
- Article
- Discovery of a lagriamide polyketide by integrated genome mining, isotopic labeling, and untargeted metabolomics.Chemical science · 2024Article
- Wakodecaline C, new tetrahydrofuran-fused decalin metabolite isolated from fungus Pyrenochaetopsis sp. RK10-F058.The Journal of antibiotics · 2023Article
- Studies on Streptomyces sp. SN-593: reveromycin biosynthesis, β-carboline biomediator activating LuxR family regulator, and construction of terpenoid biosynthetic platform.The Journal of antibiotics · 2022Review
- An integrated screening system for the selection of exemplary substrates for natural and engineered cytochrome P450s.Scientific reports · 2019Article
- Repeated evolution of cytochrome P450-mediated spiroketal steroid biosynthesis in plants.Nature communications · 2019Article
- β-carboline biomediators induce reveromycin production in Streptomyces sp. SN-593.Scientific reports · 2019Article
- Kinanthraquinone, a new anthraquinone carboxamide isolated from Streptomyces reveromyceticus SN-593-44.The Journal of antibiotics · 2018Article
- Article
- Biosynthesis of ilamycins featuring unusual building blocks and engineered production of enhanced anti-tuberculosis agents.Nature communications · 2017Article
- Competition and co-regulation of spirotoamide and tautomycetin biosynthesis in Streptomyces griseochromogenes, and isolation and structural elucidation of spirotoamide C and D.The Journal of antibiotics · 2017Article
- The Uncommon Enzymology of Cis-Acyltransferase Assembly Lines.Chemical reviews · 2017Review
- Oxidative Cyclization in Natural Product Biosynthesis.Chemical reviews · 2017Review
- In silico identification of lysocin biosynthetic gene cluster from Lysobacter sp. RH2180-5.The Journal of antibiotics · 2017Article
- A crotonyl-CoA reductase-carboxylase independent pathway for assembly of unusual alkylmalonyl-CoA polyketide synthase extender units.Nature communications · 2016Article
- Biological characterization of the hygrobafilomycin antibiotic JBIR-100 and bioinformatic insights into the hygrolide family of natural products.Bioorganic & medicinal chemistry · 2016Article
- The Draft Genome Sequence of Actinokineospora bangkokensis 44EHWMolecules (Basel, Switzerland) · 2016Article
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Authors and funding
15 authors at 6 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Spiroacetal compounds are ubiquitous in nature, and their stereospecific structures are responsible for diverse pharmaceutical activities. Elucidation of the biosynthetic mechanisms that are involved in spiroacetal formation will open the door to efficient generation of stereospecific structures that are otherwise hard to synthesize chemically. However, the biosynthesis of these compounds is poorly understood, owing to difficulties in identifying the responsible enzymes and analyzing unstable intermediates. Here we comprehensively describe the spiroacetal formation involved in the biosynthesis of reveromycin A, which inhibits bone resorption and bone metastases of tumor cells by inducing apoptosis in osteoclasts. We performed gene disruption, systematic metabolite analysis, feeding of labeled precursors and conversion studies with recombinant enzymes. We identified two key enzymes, dihydroxy ketone synthase and spiroacetal synthase, and showed in vitro reconstruction of the stereospecific spiroacetal structure from a stable acyclic precursor. Our findings provide insights into the creation of a variety of biologically active spiroacetal compounds for drug leads.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.