Literature DB >> 22047048

Type-2 isopentenyl diphosphate isomerase: evidence for a stepwise mechanism.

Nicole A Heaps1, C Dale Poulter.   

Abstract

Isopentenyl diphosphate isomerase (IDI) catalyzes the interconversion of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). These two molecules are the building blocks for construction of isoprenoid carbon skeletons in nature. Two structurally unrelated forms of IDI are known. A variety of studies support a proton addition/proton elimination mechanism for both enzymes. During studies with Thermus thermophilus IDI-2, we discovered that the olefinic hydrogens of a vinyl thiomethyl analogue of isopentenyl diphosphate exchanged with solvent when the enzyme was incubated with D(2)O without concomitant isomerization of the double bond. These results suggest that the enzyme-catalyzed isomerization reaction is not concerted.

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Year:  2011        PMID： 22047048      PMCID： PMC3237117          DOI： 10.1021/ja208331q

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  13 in total

1.  Inhibition of type 2 isopentenyl diphosphate isomerase from Methanocaldococcus jannaschii by a mechanism-based inhibitor of type 1 isopentenyl diphosphate isomerase.

Authors:  Takeshi Hoshino; Hideyuki Tamegai; Katsumi Kakinuma; Tadashi Eguchi
Journal:  Bioorg Med Chem       Date:  2006-06-21       Impact factor: 3.641

2.  Type-2 isopentenyl diphosphate isomerase. Mechanistic studies with cyclopropyl and epoxy analogues.

Authors:  Jonathan B Johnston; Joel R Walker; Steven C Rothman; C Dale Poulter
Journal:  J Am Chem Soc       Date:  2007-06-05       Impact factor: 15.419

3.  Synthesis and evaluation of chlorinated substrate analogues for farnesyl diphosphate synthase.

Authors:  Nicole A Heaps; C Dale Poulter
Journal:  J Org Chem       Date:  2011-02-24       Impact factor: 4.354

4.  Mechanism of action of isopentenyl pyrophosphate isomerase: evidence for a carbonium ion intermediate.

Authors:  J E Reardon; R H Abeles
Journal:  Biochemistry       Date:  1986-09-23       Impact factor: 3.162

5.  Catalytic mechanism of Escherichia coli isopentenyl diphosphate isomerase involves Cys-67, Glu-116, and Tyr-104 as suggested by crystal structures of complexes with transition state analogues and irreversible inhibitors.

Authors:  J Wouters; Y Oudjama; Sam J Barkley; C Tricot; V Stalon; L Droogmans; C Dale Poulter
Journal:  J Biol Chem       Date:  2003-01-22       Impact factor: 5.157

6.  Farnesyl pyrophosphate synthetase. Mechanistic studies of the 1'-4 coupling reaction with 2-fluorogeranyl pyrophosphate.

Authors:  C D Poulter; J C Argyle; E A Mash
Journal:  J Biol Chem       Date:  1978-10-25       Impact factor: 5.157

7.  Isopentenyl-diphosphate isomerase: inactivation of the enzyme with active-site-directed irreversible inhibitors and transition-state analogues.

Authors:  M Muehlbacher; C D Poulter
Journal:  Biochemistry       Date:  1988-09-20       Impact factor: 3.162

8.  Kinetic and spectroscopic characterization of type II isopentenyl diphosphate isomerase from Thermus thermophilus: evidence for formation of substrate-induced flavin species.

Authors:  Steven C Rothman; Travis R Helm; C Dale Poulter
Journal:  Biochemistry       Date:  2007-04-12       Impact factor: 3.162

9.  Crystal structure of the C67A mutant of isopentenyl diphosphate isomerase complexed with a mechanism-based irreversible inhibitor.

Authors:  J Wouters; Y Oudjama; V Stalon; L Droogmans; C D Poulter
Journal:  Proteins       Date:  2004-02-01

10.  An unusual isopentenyl diphosphate isomerase found in the mevalonate pathway gene cluster from Streptomyces sp. strain CL190.

Authors:  K Kaneda; T Kuzuyama; M Takagi; Y Hayakawa; H Seto
Journal:  Proc Natl Acad Sci U S A       Date:  2001-01-23       Impact factor: 11.205
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  4 in total

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