Literature DB >> 15381400

Enzymatic mechanisms for catalysis of enolization: ketosteroid isomerase.

Ralph M Pollack1.   

Abstract

Breaking a carbon-hydrogen bond adjacent to a carbonyl is a slow step in a large number of chemical reactions. However, many enzymes are capable of catalyzing this reaction with great efficiency. One of the most proficient of these enzymes is 3-oxo-Delta5-steroid isomerase (KSI), which catalyzes the isomerization of a wide variety of 3-oxo-Delta5-steroids to their Delta4-conjugated isomers. In this review, the mechanism of KSI is discussed, with particular emphasis on energetic considerations. Both experimental and theoretical approaches are considered to explain the mechanistic details of the reaction.

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Year:  2004        PMID: 15381400     DOI: 10.1016/j.bioorg.2004.06.005

Source DB:  PubMed          Journal:  Bioorg Chem        ISSN: 0045-2068            Impact factor:   5.275


  52 in total

1.  Evaluation of the energetics of the concerted acid-base mechanism in enzymatic catalysis: the case of ketosteroid isomerase.

Authors:  Stephen D Fried; Steven G Boxer
Journal:  J Phys Chem B       Date:  2011-12-28       Impact factor: 2.991

2.  Thermodynamic framework for identifying free energy inventories of enzyme catalytic cycles.

Authors:  Stephen D Fried; Steven G Boxer
Journal:  Proc Natl Acad Sci U S A       Date:  2013-07-09       Impact factor: 11.205

3.  Hydrogen bonding in the active site of ketosteroid isomerase: electronic inductive effects and hydrogen bond coupling.

Authors:  Philip Hanoian; Paul A Sigala; Daniel Herschlag; Sharon Hammes-Schiffer
Journal:  Biochemistry       Date:  2010-11-12       Impact factor: 3.162

4.  Kemp Eliminase Activity of Ketosteroid Isomerase.

Authors:  Vandana Lamba; Enis Sanchez; Lauren Rose Fanning; Kathryn Howe; Maria Alejandra Alvarez; Daniel Herschlag; Marcello Forconi
Journal:  Biochemistry       Date:  2017-01-20       Impact factor: 3.162

5.  Determining the catalytic role of remote substrate binding interactions in ketosteroid isomerase.

Authors:  Jason P Schwans; Daniel A Kraut; Daniel Herschlag
Journal:  Proc Natl Acad Sci U S A       Date:  2009-08-12       Impact factor: 11.205

6.  Quantum delocalization of protons in the hydrogen-bond network of an enzyme active site.

Authors:  Lu Wang; Stephen D Fried; Steven G Boxer; Thomas E Markland
Journal:  Proc Natl Acad Sci U S A       Date:  2014-12-12       Impact factor: 11.205

7.  Direct measurement of the protein response to an electrostatic perturbation that mimics the catalytic cycle in ketosteroid isomerase.

Authors:  Santosh Kumar Jha; Minbiao Ji; Kelly J Gaffney; Steven G Boxer
Journal:  Proc Natl Acad Sci U S A       Date:  2011-09-26       Impact factor: 11.205

Review 8.  Specificity in transition state binding: the Pauling model revisited.

Authors:  Tina L Amyes; John P Richard
Journal:  Biochemistry       Date:  2013-02-04       Impact factor: 3.162

Review 9.  Catalytic efficiency of enzymes: a theoretical analysis.

Authors:  Sharon Hammes-Schiffer
Journal:  Biochemistry       Date:  2012-12-20       Impact factor: 3.162

Review 10.  Fundamental challenges in mechanistic enzymology: progress toward understanding the rate enhancements of enzymes.

Authors:  Daniel Herschlag; Aditya Natarajan
Journal:  Biochemistry       Date:  2013-03-14       Impact factor: 3.162

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