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BrtB is an O-alkylating enzyme that generates fatty acid-bartoloside esters
| Resumo: | 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. © 2020, The Author(s). |
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| Assunto: | catalysis alkylating agent Alkylation carboxylic acid gene cluster halide Esters enzyme oxygen carbon enzyme activity metabolism chemical reaction Alkylating Agents chemical compound alcohol Polycyclic Aromatic Hydrocarbons Synechocystis enzymology multigene family fatty acid ester Chemistry Techniques, Synthetic catalyst nonhuman nucleophile procedures transferase chemical bonding ester alkylation polycyclic aromatic hydrocarbon Esterification fatty acid Multigene Family genetics Article nucleophilicity unclassified drug Fatty Acids bacterial protein Transferases controlled study fatty acid bartoloside ester Bacterial Proteins protein brtb chemical binding synthesis chemical bond esterification |
| País: | Portugal |
| Tipo de documento: | journal article |
| Tipo de acesso: | Aberto |
| Instituição associada: | Repositório Aberto da Universidade do Porto |
| Idioma: | inglês |
| Origem: | Repositório Aberto da Universidade do Porto |
| Resumo: | 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. © 2020, The Author(s). |
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