Study of 1-deoxy-D-xylulose-5-phosphate reductoisomerase: synthesis and evaluation of fluorinated substrate analogues

Organic Letters
Alexander WongHung-wen Liu

Abstract

[reaction: see text] 1-deoxy-D-xylulose-5-phosphate (DXP) reductoisomerase is a NADPH-dependent enzyme catalyzing the conversion of DXP to methyl-D-erythritol 4-phosphate (MEP). In this study, each of the hydroxyl groups in DXP and one of its C-1 hydrogen atoms, were separately replaced with a fluorine atom and the effect of the substitution on the catalytic turnover was examined. It was found that the 1-fluoro-DXP is a poor substrate, while both 3- and 4-fluoro-DXP behave as noncompetitive inhibitors.

References

Sep 30, 1998·Chemistry & Biology·Wolfgang EisenreichAdelbert Bacher
Oct 25, 2001·The Journal of Organic Chemistry·Brian S J Blagg, C Dale Poulter
Jan 5, 2002·Biochemistry·Andrew T KoppischC Dale Poulter
Jan 25, 2003·Antimicrobial Agents and Chemotherapy·Bertrand LellPeter Gottfried Kremsner
May 9, 2003·Natural Product Reports·Tomohisa Kuzuyama, H Seto

Citations

Oct 8, 2011·Natural Product Reports·Jeroen S Dickschat
Nov 21, 2007·The Journal of Organic Chemistry·Chandraiah LagisettiRobert M Coates
Jun 28, 2008·The Journal of Organic Chemistry·Amit KumarYashwant D Vankar

Related Concepts

YaeM protein, E coli
Catalysis
Hydrocarbons, Fluorinated
Multienzyme Complexes
Oxidase
Substrate Specificity
Aldose-Ketose Isomerases

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