Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 32, Pages 10972-10975Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b05060
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Funding
- National Science Foundation [CHE 1152055, CBET 1336636]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1608553] Funding Source: National Science Foundation
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Ferulic acid decarboxylase catalyzes the decarboxylation of phenylacrylic acid using a newly identified cofactor, prenylated flavin mononucleotide (prFMN). The proposed mechanism involves the formation of a putative pentacyclic intermediate formed by a 1,3 dipolar cyclo-addition of prFMN with the alpha-beta double bond of the substrate, which serves to activate the substrate toward decarboxylation. However, enzyme catalyzed 1,3 dipolar cyclo-additions are unprecedented and other mechanisms are plausible. Here we describe the use of a mechanism-based inhibitor, 2-fluoro-2-nitro-vinylbenzene, to trap the putative cyclo-addition intermediate, thereby demonstrating that prFMN can function as a dipole in a 1,3 dipolar cyclo-addition reaction as the initial step in a novel type of enzymatic reaction.
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