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Hydrolysis of phenylacetanilides catalyzed by penicillin G acylase from Alcaligenes faecalis: Sensitivity of the reaction to substitution in the leaving group

Paper ID Volume ID Publish Year Pages File Format Full-Text
52533 46876 2009 6 PDF Available
Title
Hydrolysis of phenylacetanilides catalyzed by penicillin G acylase from Alcaligenes faecalis: Sensitivity of the reaction to substitution in the leaving group
Abstract

The paper presents kinetic results on the hydrolysis of a series of p-substituted anilides catalyzed by penicillin G acylase from Alcaligenes faecalis. They are compared to the highly identical Escherichia coli enzyme and in combination with a structural model will contribute to deeper understanding of the catalytic mechanism and energetics of the reaction of the N-terminal-nucleophile superfamily. The Hammett plot indicates that acylation is the rate-limiting stage of hydrolysis. The collapse of the tetrahedral intermediate proceeds via synchronous bond breaking and formation, and the accumulation of charge on the amidic nitrogen due to the presence of a substituent is disfavored.

Keywords
Ec-PGA (Af-PGA), penicillin G acylase from Escherichia coli (Alcaligenes faecalis); Ntn, N-terminal nucleophile; TI, tetrahedral intermediate; TS, transition state; AE, acyl-enzyme; GGT, γ-glutamyl transpeptidase; AGA, aspartylglucosaminidasePenicillin G
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Hydrolysis of phenylacetanilides catalyzed by penicillin G acylase from Alcaligenes faecalis: Sensitivity of the reaction to substitution in the leaving group
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 11, Issue 3, 25 November 2009, Pages 196–201
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Price was $35.95
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Full-text PDF Download
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