Literature DB >> 16321020

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

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

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.

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Year:  2005        PMID： 16321020     DOI： 10.1021/ol0524050

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 in total

1.  New role of flavin as a general acid-base catalyst with no redox function in type 2 isopentenyl-diphosphate isomerase.

Authors:  Hideaki Unno; Satoshi Yamashita; Yosuke Ikeda; Shin-Ya Sekiguchi; Norie Yoshida; Tohru Yoshimura; Masami Kusunoki; Toru Nakayama; Tokuzo Nishino; Hisashi Hemmi
Journal:  J Biol Chem       Date:  2009-01-21       Impact factor: 5.157

Review 2.  Mechanistic aspects of carotenoid biosynthesis.

Authors:  Alexander R Moise; Salim Al-Babili; Eleanore T Wurtzel
Journal:  Chem Rev       Date:  2013-10-31       Impact factor: 60.622

3.  Linear free energy relationships demonstrate a catalytic role for the flavin mononucleotide coenzyme of the type II isopentenyl diphosphate:dimethylallyl diphosphate isomerase.

Authors:  Christopher J Thibodeaux; Wei-chen Chang; Hung-wen Liu
Journal:  J Am Chem Soc       Date:  2010-07-28       Impact factor: 15.419

4.  Stereochemical studies of the type II isopentenyl diphosphate-dimethylallyl diphosphate isomerase implicate the FMN coenzyme in substrate protonation.

Authors:  Jordi Calveras; Christopher J Thibodeaux; Steven O Mansoorabadi; Hung-wen Liu
Journal:  Chembiochem       Date:  2011-12-01       Impact factor: 3.164

5.  Covalent modification of reduced flavin mononucleotide in type-2 isopentenyl diphosphate isomerase by active-site-directed inhibitors.

Authors:  Takuya Nagai; Hideaki Unno; Matthew Walter Janczak; Tohru Yoshimura; C Dale Poulter; Hisashi Hemmi
Journal:  Proc Natl Acad Sci U S A       Date:  2011-12-07       Impact factor: 11.205

Review 6.  Methylerythritol phosphate pathway of isoprenoid biosynthesis.

Authors:  Lishan Zhao; Wei-chen Chang; Youli Xiao; Hung-wen Liu; Pinghua Liu
Journal:  Annu Rev Biochem       Date:  2013       Impact factor: 23.643

Review 7.  The type II isopentenyl Diphosphate:Dimethylallyl diphosphate isomerase (IDI-2): A model for acid/base chemistry in flavoenzyme catalysis.

Authors:  Christopher J Thibodeaux; Hung-Wen Liu
Journal:  Arch Biochem Biophys       Date:  2017-05-31       Impact factor: 4.013

8.  Evidence for the involvement of acid/base chemistry in the reaction catalyzed by the type II isopentenyl diphosphate/dimethylallyl diphosphate isomerase from Staphylococcus aureus.

Authors:  Christopher J Thibodeaux; Steven O Mansoorabadi; William Kittleman; Wei-chen Chang; Hung-wen Liu
Journal:  Biochemistry       Date:  2008-01-30       Impact factor: 3.162

Review 9.  The diverse roles of flavin coenzymes--nature's most versatile thespians.

Authors:  Steven O Mansoorabadi; Christopher J Thibodeaux; Hung-wen Liu
Journal:  J Org Chem       Date:  2007-06-20       Impact factor: 4.354

10.  Characterization and mechanistic studies of type II isopentenyl diphosphate:dimethylallyl diphosphate isomerase from Staphylococcus aureus.

Authors:  William Kittleman; Christopher J Thibodeaux; Yung-nan Liu; Hua Zhang; Hung-wen Liu
Journal:  Biochemistry       Date:  2007-06-22       Impact factor: 3.162
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