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Brief history of glyoxalase I and what we have learned about metal ion-dependent, enzyme-catalyzed isomerizations.

Abstract：

:Glyoxalase I, a member of the metalloglutathione (GSH) transferase superfamily, plays a critical detoxification role in cells by catalyzing the conversion of cytotoxic methylglyoxal (as the diastereomeric GSH-thiohemiacetals) to S-D-lactoylglutathione via a 1,2-hydrogen transfer. The mechanism-of-action of this Zn2+-metalloenzyme has been the subject of considerable controversy over the past 50 years. Key issues relate to the role of the active-site metal ion in catalysis and how the enzyme is able to use directly both diastereomeric thiohemiacetals as substrates. The results of recent X-ray crystallographic measurements on the enzyme in complex with a transition state analogue and site-directed mutagenesis studies now strongly support a base-mediated, proton-transfer mechanism in which the bound diastereomeric substrates undergo catalytic interconversion before the 1S-diastereomer goes to product via a Zn2+-coordinated, cis-enediolate intermediate. Comparisons with chemical model systems suggest that Zn2+-coordination of thiohemiacetal substrate will dramatically increase the thermodynamic and kinetic acidity of the C1-H bond of substrate. In the human enzyme, the carboxyl group of Glu (172) is well positioned to catalyze a suprafacial proton transfer between the adjacent carbons of substrate. The Zn2+-coordinated carboxyl group of Glu(99) is a reasonable candidate to catalyze proton transfer between the Zn2+-coordinated oxygen atoms of the enediolate intermediate. Other Zn2+ metalloenzymes appear to use similar reaction mechanisms to facilitate proton transfers.

journal_name

Arch Biochem Biophys

journal_title

Archives of biochemistry and biophysics

authors

Creighton DJ,Hamilton DS

doi

10.1006/abbi.2000.2253

subject

Has Abstract

pub_date

2001-03-01 00:00:00

pages

1-10

issue

1

eissn

0003-9861

issn

1096-0384

pii

S0003-9861(00)92253-7

journal_volume

387

pub_type

杂志文章,评审

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