Substrate analogs for the investigation of deoxyxylulose 5-phosphate reductoisomerase inhibition: synthesis and evaluation

Bioorganic & Medicinal Chemistry Letters
2004.0

Abstract

Deoxyxylulose 5-phosphate (DXP) analogs were synthesized and evaluated as alternative substrates and inhibitors of recombinant Synechocystis PCC6803 DXP reductoisomerase (DXR; EC 1.1.1.267). Five of the compounds tested (1,2-dideoxy-D-threo-3-hexulose 6-phosphate, 1-deoxy-l-ribulose 5-phosphate, 2S,3R-dihydroxybutyramide 4-phosphate, 4S-hydroxypentan-2-one 5-phosphate, and 3S-hydroxypentan-2-one 5-phosphate) acted as relatively weak competitive inhibitors when compared to fosmidomycin. A sixth compound, 3R,4S-dihydroxy-5-oxohexylphosphonic acid, served as an alternate substrate, as has recently been reported for the same compound with Escherichia coli DXR.

Knowledge Graph

Similar Paper

Substrate analogs for the investigation of deoxyxylulose 5-phosphate reductoisomerase inhibition: synthesis and evaluation
Bioorganic & Medicinal Chemistry Letters 2004.0
Synthesis and biological evaluation of phosphate isosters of fosmidomycin and analogs as inhibitors of Escherichia coli and Mycobacterium smegmatis 1-deoxyxylulose 5-phosphate reductoisomerases
Bioorganic & Medicinal Chemistry 2017.0
Catechol–rhodanine derivatives: Specific and promiscuous inhibitors of Escherichia coli deoxyxylulose phosphate reductoisomerase (DXR)
Bioorganic & Medicinal Chemistry 2014.0
Design, Synthesis, and X-ray Crystallographic Studies of α-Aryl Substituted Fosmidomycin Analogues as Inhibitors of Mycobacterium tuberculosis 1-Deoxy-<scp>d</scp>-xylulose 5-Phosphate Reductoisomerase
Journal of Medicinal Chemistry 2011.0
Coordination Chemistry Based Approach to Lipophilic Inhibitors of 1-Deoxy-<scp>d</scp>-xylulose-5-phosphate Reductoisomerase
Journal of Medicinal Chemistry 2009.0
Non-hydroxamate inhibitors of 1-deoxy-d-xylulose 5-phosphate reductoisomerase (DXR): A critical review and future perspective
European Journal of Medicinal Chemistry 2021.0
Synthesis and Bioactivity of β-Substituted Fosmidomycin Analogues Targeting 1-Deoxy-<scp>d</scp>-xylulose-5-phosphate Reductoisomerase
Journal of Medicinal Chemistry 2015.0
Synthesis and evaluation of phosphonated N-heteroarylcarboxamides as DOXP-reductoisomerase (DXR) inhibitors
Bioorganic &amp; Medicinal Chemistry 2011.0
Inhibition of 1-Deoxy-<scp>d</scp>-Xylulose-5-Phosphate Reductoisomerase by Lipophilic Phosphonates: SAR, QSAR, and Crystallographic Studies
Journal of Medicinal Chemistry 2011.0
Synthesis of tetrazole analogues of phosphonohydroxamic acids: An attempt to improve the inhibitory activity against the DXR
Bioorganic &amp; Medicinal Chemistry Letters 2013.0