PMID: 6989412Apr 1, 1980Paper

Hydrophobic binding is not an independent stereochemical determinant in the yeast glyoxalase I reaction

Biophysical Chemistry
D J CreightonL Buettner

Abstract

For yeast glyoxalase I, a stereospecific proton-transfer mechanism requires the formation of either a cis or a trans-enediol intermediate. Analogs of the two possible isometric enediol intermediates, formed from the hemimercaptal due to phenylglyoxal and glutathione, have been synthesized in which the oxygen atoms of the enediol are replaced by protons. Both isomeric analogs are strong linear competitive inhibitors of the enzyme having nearly equal inhibition constants: Ki(cis) = 0.10 mM; Ki(trans) = 0.16 mM. This suggests that while hydrophobic interactions between substrate, enediol intermediate and enzyme may contribute significantly to binding, this type of interaction is not an independent stereochemical determinant of the reaction.

References

Apr 28, 1978·Biochemical and Biophysical Research Communications·A C AronssonB Mannervik
Nov 10, 1976·Journal of the American Chemical Society·S S HallF Jordan
May 1, 1971·Journal of Medicinal Chemistry·R VinceW B Wadd
May 1, 1971·Analytical Biochemistry·N M Alexander, J L Boyer
Jan 1, 1957·The Biochemical Journal·W O KERMACK, N A MATHESON
Jul 1, 1957·Biochimica Et Biophysica Acta·I A Rose

Citations

Jan 1, 1983·Drug Metabolism Reviews·F JordanD L Foxall
Jun 7, 1983·Biochemistry·C E GriffisD J Creighton

Related Concepts

Reduced Glutathione
Lactoylglutathione Lyase
Desmolases
Plasma Protein Binding Capacity
Oxopropanal
Saccharomyces cerevisiae

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