ArticleJournal of the American Chemical Society2017
Biosynthesis of Branched Alkoxy Groups: Iterative Methyl Group Alkylation by a Cobalamin-Dependent Radical SAM Enzyme.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.
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Who cites it
35 citing papers in PubMed, 68 citations in OpenAlex.
- Beyond native reactivity: radical SAM enzymes as platforms for new-to-nature chemistry.RSC chemical biology · 2026Review
- Novel chemistry and structural perspectives in vitamin BChemical science · 2026Review
- Structural basis for iterative methylation by a cobalamin-dependent radicalProceedings of the National Academy of Sciences of the United States of America · 2026Article
- Structural Basis for Iterative Methylation by a Cobalamin-dependent Radical S-Adenosylmethionine Enzyme in Cystobactamids Biosynthesis.bioRxiv : the preprint server for biology · 2025Article
- Radical Fluoromethylation Enabled by Cobalamin-Dependent Radical SAM Enzymes.ACS bio & med chem Au · 2025Article
- Initiation, Propagation, and Termination in the Chemistry of Radical SAM Enzymes.Biochemistry · 2024Review
- Changing Fates of the Substrate Radicals Generated in the Active Sites of the BJournal of the American Chemical Society · 2023Article
- ThnL, a B12-dependent radicalProceedings of the National Academy of Sciences of the United States of America · 2022Article
- A Cobalamin-Dependent Radical SAM Enzyme Catalyzes the Unique CAngewandte Chemie (International ed. in English) · 2022Article
- Stereochemical course of cobalamin-dependent radical SAM methylation by TokK and ThnK.RSC chemical biology · 2022Article
- Biosynthesis of 3-thia-α-amino acids on a carrier peptide.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
- Cobalamin-Dependent RadicalACS bio & med chem Au · 2022Review
- The Atypical Cobalamin-DependentJournal of the American Chemical Society · 2022Article
- Evolution of Methods for the Study of Cobalamin-Dependent Radical SAM Enzymes.ACS bio & med chem Au · 2022Article
- Crystallographic snapshots of a BNature · 2022Article
- Structure of a BNature · 2022Article
- Purification and characterization of sequential cobalamin-dependent radical SAM methylases ThnK and TokK in carbapenem β-lactam antibiotic biosynthesis.Methods in enzymology · 2022Article
- Studies of GenK and OxsB, two BMethods in enzymology · 2022Article
- Overall Retention of Methyl Stereochemistry during BBiochemistry · 2021Article
- Biosynthesis of Oxetanocin-A Includes a BBiochemistry · 2021Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
The biosynthesis of branched alkoxy groups, such as the unique t-butyl group found in a variety of natural products, is still poorly understood. Recently, cystobactamids were isolated and identified from Cystobacter sp as novel antibacterials. These metabolites contain an isopropyl group proposed to be formed using CysS, a cobalamin-dependent radical S-adenosylmethionine (SAM) methyltransferase. Here, we reconstitute the CysS-catalyzed reaction, on p-aminobenzoate thioester substrates, and demonstrate that it not only catalyzes sequential methylations of a methyl group to form ethyl and isopropyl groups but remarkably also sec-butyl and t-butyl groups. To our knowledge, this is the first in vitro reconstitution of a cobalamin-dependent radical SAM enzyme catalyzing the conversion of a methyl group to a t-butyl group.
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Registered trials
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.