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The mechanism of sugar phosphate isomerization by glucosamine 6-phosphate synthase

Published online by Cambridge University Press:  01 March 1999

ALEXEI TEPLYAKOV
Affiliation:
Genetics and Biochemistry Branch, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892
GALYA OBMOLOVA
Affiliation:
Genetics and Biochemistry Branch, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892
MARIE-ANGE BADET-DENISOT
Affiliation:
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France
BERNARD BADET
Affiliation:
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France
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Abstract

Glucosamine 6-phosphate synthase converts fructose-6P into glucosamine-6P or glucose-6P depending on the presence or absence of glutamine. The isomerase activity is associated with a 40-kDa C-terminal domain, which has already been characterized crystallographically. Now the three-dimensional structures of the complexes with the reaction product glucose-6P and with the transition state analog 2-amino-2-deoxyglucitol-6P have been determined. Glucose-6P binds in a cyclic form whereas 2-amino-2-deoxyglucitol-6P is in an extended conformation. The information on ligand-protein interactions observed in the crystal structures together with the isotope exchange and site-directed mutagenesis data allow us to propose a mechanism of the isomerase activity of glucosamine-6P synthase. The sugar phosphate isomerization involves a ring opening step catalyzed by His504 and an enolization step with Glu488 catalyzing the hydrogen transfer from C1 to C2 of the substrate. The enediol intermediate is stabilized by a helix dipole and the ε-amino group of Lys603. Lys485 may play a role in deprotonating the hydroxyl O1 of the intermediate.

Type
Research Article
Copyright
© 1999 The Protein Society

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