ArticleJournal of the American Chemical Society2010
A biosynthetic pathway for BE-7585A, a 2-thiosugar-containing angucycline-type natural product.
Article in Journal of the American Chemical Society, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed, 67 citations in OpenAlex.
- (+)-BE-7585A and its derhodinosyl derivative, two cytotoxic 2-thiosugar-containing angucyclines, derived from an actinomycete Amycolatopsis sp. JS6.The Journal of antibiotics · 2026Article
- In Vitro Characterization of Kitasetaline Biosynthesis Reveals a Bifunctional P450 Decarboxylase and a Vinyl β-Carboline Intermediate Susceptible to Nonenzymatic Thiol Addition.Journal of the American Chemical Society · 2024Article
- Capability of a large bacterial artificial chromosome clone harboring multiple biosynthetic gene clusters for the production of diverse compounds.The Journal of antibiotics · 2024Article
- CompleteJournal of the American Chemical Society · 2024Article
- The many facets of sulfur incorporation in natural product biosynthesis.Current opinion in chemical biology · 2023Review
- Characterization of the Biosynthetic Gene Cluster and Shunt Products Yields Insights into the Biosynthesis of Balmoralmycin.Applied and environmental microbiology · 2022Article
- Microbiological versus Chemical Reductive Sulfidation: An Experimental and Theoretical Study.ACS omega · 2021Article
- Cryptic Sulfur Incorporation in Thioangucycline Biosynthesis.Angewandte Chemie (International ed. in English) · 2021Article
- Biosynthesis of Diverse Type II Polyketide Core Structures inACS synthetic biology · 2021Article
- Discovery of Mycothiogranaticins from Streptomyces vietnamensis GIMV4.0001 and the Regulatory Effect of Mycothiol on the Granaticin Biosynthesis.Frontiers in chemistry · 2021Article
- Baikalomycins A-C, New Aquayamycin-Type Angucyclines Isolated from Lake Baikal DerivedMicroorganisms · 2020Article
- Computational identification of co-evolving multi-gene modules in microbial biosynthetic gene clusters.Communications biology · 2019Article
- Comparative Genomics and Biosynthetic Potential Analysis of Two Lichen-IsolatedFrontiers in microbiology · 2018Article
- Two Cooperative Glycosyltransferases Are Responsible for the Sugar Diversity of Saquayamycins Isolated from Streptomyces sp. KY 40-1.ACS chemical biology · 2017Article
- Formation of an Angular Aromatic Polyketide from a Linear Anthrene Precursor via Oxidative Rearrangement.Cell chemical biology · 2017Article
- Oxidative Cyclization in Natural Product Biosynthesis.Chemical reviews · 2017Review
- The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems.Angewandte Chemie (International ed. in English) · 2017Review
- Insights into Complex Oxidation during BE-7585A Biosynthesis: Structural Determination and Analysis of the Polyketide Monooxygenase BexE.ACS chemical biology · 2016Article
- Structural and functional analysis of two di-domain aromatase/cyclases from type II polyketide synthases.Proceedings of the National Academy of Sciences of the United States of America · 2015Article
- A comprehensive review of glycosylated bacterial natural products.Chemical Society reviews · 2015Review
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3 authors at 1 institution in 1 country.
Funding
Abstract
Sulfur is an essential element found ubiquitously in living systems. However, there exist only a few sulfur-containing sugars in nature and their biosyntheses have not been studied. BE-7585A produced by Amycolatopsis orientalis subsp. vinearia BA-07585 has a 2-thiosugar and is a member of the angucycline class of compounds. We report herein the results of our initial efforts to study the biosynthesis of BE-7585A. Spectroscopic analyses verified the structure of BE-7585A, which is closely related to rhodonocardin A. Feeding experiments using (13)C-labeled acetate were carried out to confirm that the angucycline core is indeed polyketide-derived. The results indicated an unusual manner of angular tetracyclic ring construction, perhaps via a Baeyer-Villiger type rearrangement. Subsequent cloning and sequencing led to the identification of the bex gene cluster spanning approximately 30 kbp. A total of 28 open reading frames, which are likely involved in BE-7585A formation, were identified in the cluster. In view of the presence of a homologue of a thiazole synthase gene (thiG), bexX, in the bex cluster, the mechanism of sulfur incorporation into the 2-thiosugar moiety could resemble that found in thiamin biosynthesis. A glycosyltransferase homologue, BexG2, was heterologously expressed in Escherichia coli. The purified enzyme successfully catalyzed the coupling of 2-thioglucose 6-phosphate and UDP-glucose to produce 2-thiotrehalose 6-phosphate, which is the precursor of the disaccharide unit in BE-7585A. On the basis of these genetic and biochemical experiments, a biosynthetic pathway for BE-7585A can now be proposed. The combined results set the stage for future biochemical studies of 2-thiosugar biosynthesis and BE-7585A assembly.
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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.