Reinvestigation of the roles of the carboxyl groups of glutathione with yeast glyoxalase I
- 7 July 1986
- journal article
- Published by Wiley in FEBS Letters
- Vol. 202 (2) , 240-244
- https://doi.org/10.1016/0014-5793(86)80694-9
Abstract
A number of carboxyl-substituted s-blocked glutathiones have been shown to be competitive inhibitors of yeast glyoxalase I at 25°C, pH 6.6. Amidation of the glycyl carboxyl group of S-(p-bromobenzyl)glutathione has no appreciable effect on binding whilst methylation reduces binding by 8.9-fold, indicating a steric constraint and the possible presence of a hydrogen bond in this region of the enzyme. Amidation of both carboxyl groups of S-(p-bromobenzyl)glutathione reduces binding significantly by 237-fold; this result agrees with electrostatic interaction of the Glu COO− group with a group located within the enzyme surface as opposed to the Gly COO− group, previously proposed.Keywords
This publication has 16 references indexed in Scilit:
- Involvement of arginine residues in glutathione binding to yeast glyoxalase IBiochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology, 1983
- Direct demonstration by1H n.m.r. spectrometry of the stereoselectivity of yeast glyoxalase I towards the diastereomeric forms of the α-ketoaldehyde–glutathione hemithioacetalJournal of the Chemical Society, Chemical Communications, 1981
- Glyoxalase I enzyme studies. 4. General base catalyzed enediol proton transfer rearrangement of methyl- and phenylglyoxalglutathionylhemithiol acetal to S-lactoyl- and S-mandeloylglutathione followed by hydrolysis. A model for the glyoxalase enzyme systemJournal of the American Chemical Society, 1978
- Deuterium isotope effects and chemically modified coenzymes as mechanism probes of yeast glyoxalase-IBiochemistry, 1973
- Glutaryl-S-(p-bromobenzyl)-L-cysteinylglycine. Metabolically stable inhibitor of glyoxalase IJournal of Medicinal Chemistry, 1973
- [9] HydrazinolysisPublished by Elsevier ,1972
- Inhibition of glyoxalase I by S-substituted glutathionesJournal of Medicinal Chemistry, 1971
- Glyoxalase inhibitors. A possible approach to anticancer agentsJournal of Medicinal Chemistry, 1971
- BioelectronicsScience, 1968
- Über Die Konfiguration des Glutathions aus Tumoren: II. Mitteilung über die Chemie der TumorenRecueil des Travaux Chimiques des Pays-Bas, 1946