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• W2334656988 endingPage "6583" @default.
• W2334656988 startingPage "6574" @default.
• W2334656988 abstract "The flavin-mediated enzymatic oxidation of a CN bond in amino acids can occur through hydride transfer, carbanion, or polar nucleophilic mechanisms. Previous results with d-arginine dehydrogenase from Pseudomonas aeruginosa (PaDADH) using multiple deuterium kinetic isotope effects (KIEs) and computational studies established preferred binding of the substrate protonated on the α-amino group, with cleavages of the NH and CH bonds occurring in asynchronous fashion, consistent with the three possible mechanisms. The hydroxyl groups of Y53 and Y249 are ≤4 Å from the imino and carboxylate groups of the reaction product iminoarginine, suggesting participation in binding and catalysis. In this study, we have investigated the reductive half-reactions of the Y53F and Y249F variants of PaDADH using substrate and solvent deuterium KIEs, solvent viscosity and pH effects, and quantum mechanical/molecular mechanical computational approaches to gain insights into the catalytic roles of the tyrosines and evaluate whether their mutations affect the transition state for substrate oxidation. Both Y53F and Y249F enzymes oxidized d-arginine with steady-state kinetic parameters similar to those of the wild-type enzyme. Rate constants for flavin reduction (kred) with d-leucine, a slow substrate amenable to rapid kinetics, were 3-fold smaller than the wild-type value with similar pKa values for an unprotonated group of ∼10.0. Similar pKa values were observed for appKd in the variant and wild-type enzymes. However, cleavage of the substrate NH and CH bonds in the enzyme variants occurred in synchronous fashion, as suggested by multiple deuterium KIEs on kred. These data can be reconciled with a hydride transfer mechanism, but not with carbanion and polar nucleophilic mechanisms." @default.
• W2334656988 created "2016-06-24" @default.
• W2334656988 creator A5023523841 @default.
• W2334656988 creator A5032766595 @default.
• W2334656988 creator A5043343120 @default.
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• W2334656988 date "2014-10-07" @default.
• W2334656988 modified "2023-09-25" @default.
• W2334656988 title "Mechanistic and Computational Studies of the Reductive Half-Reaction of Tyrosine to Phenylalanine Active Site Variants of <scp>d</scp>-Arginine Dehydrogenase" @default.
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• W2334656988 doi "https://doi.org/10.1021/bi500917q" @default.
• W2334656988 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25243743" @default.
• W2334656988 hasPublicationYear "2014" @default.
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