title: Stereochemical analysis of isopentenyl diphosphate isomerase type II from Staphylococcus aureus using chemically synthesized (S)- and (R)-[2-2H]isopentenyl diphosphates.
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.
authors.affiliation: Division of Medicinal Chemistry, College of Pharmacy and Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Chai-lin
authors.initials: CL
authors.lastname: Kao
authors.forename: William
authors.initials: W
authors.lastname: Kittleman
authors.forename: Hua
authors.initials: H
authors.lastname: Zhang
authors.forename: Haruo
authors.initials: H
authors.lastname: Seto
authors.forename: Hung-wen
authors.initials: HW
authors.lastname: Liu
mesh_terms: D019748:Carbon-Carbon Double Bond Isomerases / Q000032:analysis / Q000378:metabolism*; D002384:Catalysis; D005420:Flavoproteins / Q000032:analysis / Q000378:metabolism*; D045782:Hemiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013211:Staphylococcus aureus / Q000201:enzymology*; D013237:Stereoisomerism
chemical_list: D005420:Flavoproteins; D045782:Hemiterpenes; D009943:Organophosphorus Compounds; C004809:isopentenyl pyrophosphate; D019748:Carbon-Carbon Double Bond Isomerases; C021453:isopentenyldiphosphate delta-isomerase