BrtB is an O-alkylating enzyme that generates fatty acid-bartoloside esters
2020
Reis, J.P.A | Figueiredo, S.A.C | Sousa, M.L | Leão, P.N. | Centro Interdisciplinar de Investigação Marinha e Ambiental
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).
Afficher plus [+] Moins [-]We acknowledge funding by the European Research Council, through a Starting Grant (Grant Agreement 759840) to P.N.L., and by Fundação para a Ciência e Tecnologia (FCT) through project PTDC/BIA-BQM/29710/2017 and grant IF/01358/2014 to P.N.L. The work was also partially supported by Strategic Funding UIDB/04423/2020 and UIDP/04423/2020 by FCT and the European Regional Development Fund, as part of the program PT2020. We thank Emily Balskus (Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA, USA) for helpful discussions and Ralph Urbatzka (CIIMAR, University of Porto, Porto, Portugal) for help with cytotoxicity assays.
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