Stereochemical analysis of isopentenyl diphosphate isomerase type II from Staphylococcus aureus using chemically synthesized (S)- and (R)-[2-2H]isopentenyl diphosphates

Chai-lin Kao; William Kittleman; Hua Zhang; Haruo Seto; Hung-wen Liu

doi:10.1021/ol0524050

Stereochemical analysis of isopentenyl diphosphate isomerase type II from Staphylococcus aureus using chemically synthesized (S)- and (R)-[2-2H]isopentenyl diphosphates

Org Lett. 2005 Dec 8;7(25):5677-80. doi: 10.1021/ol0524050.

Authors

Chai-lin Kao¹, William Kittleman, Hua Zhang, Haruo Seto, Hung-wen Liu

Affiliation

¹ Division of Medicinal Chemistry, College of Pharmacy and Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA.

PMID: 16321020
DOI: 10.1021/ol0524050

Abstract

[chemical reaction: see text]. To study the catalysis of isopentenyl diphosphate (IPP) isomerase type II from Staphylococcus aureus, which is a flavoprotein catalyzing the interconversion of IPP and dimethylallyl diphosphate, we have chemically synthesized (S)- and (R)-[2-2H]IPP and carried out stereochemical analysis of the reaction. Our results show that the C-2 deprotonation of IPP by this enzyme is pro-R stereospecific, suggesting a similar stereochemical course as the type I enzyme.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbon-Carbon Double Bond Isomerases / analysis
Carbon-Carbon Double Bond Isomerases / metabolism*
Catalysis
Flavoproteins / analysis
Flavoproteins / metabolism*
Hemiterpenes / chemical synthesis*
Hemiterpenes / chemistry
Molecular Structure
Organophosphorus Compounds / chemical synthesis*
Organophosphorus Compounds / chemistry
Staphylococcus aureus / enzymology*
Stereoisomerism

Substances

Flavoproteins
Hemiterpenes
Organophosphorus Compounds
isopentenyl pyrophosphate
Carbon-Carbon Double Bond Isomerases
isopentenyldiphosphate delta-isomerase