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FEBS J. 2010 Apr;277(7):1738-46. doi: 10.1111/j.1742-4658.2010.07597.x. Epub 2010 Feb 23.

On the thermodynamic equilibrium between (R)-2-hydroxyacyl-CoA and 2-enoyl-CoA.

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1
Laboratory for Microbiology, Philipps-Universit├Ąt, Marburg, Germany.

Abstract

A combined experimental and computational approach has been applied to investigate the equilibria between several alpha-hydroxyacyl-CoA compounds and their 2-enoyl-CoA derivatives. In contrast to those of their beta, gamma and delta counterparts, the equilibria for the alpha-compounds are relatively poorly characterized, but qualitatively they appear to be unusually sensitive to substituents. Using a variety of techniques, we have succeeded in measuring the equilibrium constants for the reactions beginning from 2-hydroxyglutaryl-CoA and lactyl-CoA. A complementary computational evaluation of the equilibrium constants shows quantitative agreement with the measured values. By examining the computational results, we arrive at an explanation of the substituent sensitivity and provide a prediction for the, as yet unmeasured, equilibrium involving 2-hydroxyisocaproyl-CoA.

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