ArticleNature communications2020
BrtB is an O-alkylating enzyme that generates fatty acid-bartoloside esters.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Biochemical Studies of a Cyanobacterial Halogenase Support the Involvement of a Dimetal Cofactor.Biochemistry · 2025Article
- Isolation and Biosynthesis of Hyellamide, a Glycosylated N-Acyltyrosine Derivative, from the CyanobacteriumJournal of natural products · 2025Article
- Chemical diversity of cyanobacterial natural products.Natural product reports · 2025Review
- Expanding the Diversity of the Cyanobacterial Dialkylresorcinol Bartoloside Family.Journal of natural products · 2024Article
- Accelerating the discovery of alkyl halide-derived natural products using halide depletion.Nature chemistry · 2024Article
- Incorporation and modification of fatty acids in cyanobacterial natural products biosynthesis.Chemical communications (Cambridge, England) · 2023Review
- Incorporation, fate, and turnover of free fatty acids in cyanobacteria.FEMS microbiology reviews · 2023Review
- Structural basis for an unprecedented enzymatic alkylation in cylindrocyclophane biosynthesis.eLife · 2022Article
- Cryptic halogenation reactions in natural product biosynthesis.Natural product reports · 2021Review
- Article
- Discovery of Cyanobacterial Natural Products Containing Fatty Acid Residues*.Angewandte Chemie (International ed. in English) · 2021Article
- Biosynthesis of Chlorinated Lactylates inJournal of natural products · 2021Article
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Authors and funding
4 authors.
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Abstract
Esterification reactions are central to many aspects of industrial and biological chemistry. The formation of carboxyesters typically occurs through nucleophilic attack of an alcohol onto the carboxylate carbon. Under certain conditions employed in organic synthesis, the carboxylate nucleophile can be alkylated to generate esters from alkyl halides, but this reaction has only been observed transiently in enzymatic chemistry. Here, we report a carboxylate alkylating enzyme - BrtB - that catalyzes O-C bond formation between free fatty acids of varying chain length and the secondary alkyl halide moieties found in the bartolosides. Guided by this reactivity, we uncovered a variety of natural fatty acid-bartoloside esters, previously unrecognized products of the bartoloside biosynthetic gene cluster.
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