PMID:20369853

Citation	Mukherjee, T, Zhang, Y, Abdelwahed, S, Ealick, SE and Begley, TP (2010) Catalysis of a flavoenzyme-mediated amide hydrolysis. J. Am. Chem. Soc. 132:5550-1
Abstract	A new pyrimidine catabolic pathway (the Rut pathway) was recently discovered in Escherichia coli K12. In this pathway, uracil is converted to 3-hydroxypropionate, ammonia, and carbon dioxide. The seven-gene Rut operon is required for this conversion. Here we demonstrate that the flavoenzyme RutA catalyzes the initial uracil ring-opening reaction to give 3-ureidoacrylate. This reaction, while formally a hydrolysis reaction, proceeds by an oxidative mechanism initiated by the addition of a flavin hydroperoxide to the C4 carbonyl. While peroxide-catalyzed amide hydrolysis has chemical precedent, we are not aware of a prior example of analogous chemistry catalyzed by flavin hydroperoxides. This study further illustrates the extraordinary catalytic versatility of the flavin cofactor.
Links	PubMed PMC2873085 Online version:10.1021/ja9107676
Keywords	Acrylates/chemistry; Acrylates/metabolism; Amides/metabolism; Biocatalysis; Flavin-Adenine Dinucleotide/metabolism; Hydrolysis; Models, Molecular; Oxidation-Reduction; Oxidoreductases/metabolism; Protein Conformation
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