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BrtB Is a Novel O-Alkylating Enzyme That Generates Fatty Acid-Bartoloside Esters

preprint
submitted on 01.08.2019 and posted on 02.08.2019 by João P. A. Reis, Sandra A. C. Figueiredo, Pedro Leao
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 new carboxylate alkylating enzyme – BrtB – that catalyzes O-C bond formation between free fatty acids and the secondary alkyl halide moieties found in the bartolosides. Guided by this novel reactivity, we uncovered a variety of natural fatty acid-bartoloside esters, the likely end-products of bartoloside biosynthetic gene clusters.

Funding

European Research Council (ERC Grant Agreement 759840)

Fundação para a Ciência e a Tecnologia (PTDC/BIA-BQM/29710/2017)

Fundação para a Ciência e a Tecnologia (IF/01358/2014)

Fundação para a Ciência e a Tecnologia (UID/Multi/04423/2013 Strategic Funding)

History

Email Address of Submitting Author

pleao@ciimar.up.pt

Institution

CIIMAR - University of Porto

Country

Portugal

ORCID For Submitting Author

0000-0001-5064-9164

Declaration of Conflict of Interest

No conflict of interest.

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