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Research article - Peer-reviewed, 2005

Synthesis of 5-deoxy-5-phospho-D-ribonohydroxamic acid: a new competitive and selective inhibitor of type B ribose-5-phosphate isomerase from Mycobacterium tuberculosis

Burgos E, Roos AK, Mowbray SL, Salmon L


5-Deoxy-5-phospho-D-ribonohydroxamic acid, a mimic of the 1,2-cis-enediolate high-energy intermediate species of the allose-6-phosphate isomerase reaction, was obtained by a six-step synthesis from D-erythronolactone. In contrast to the known competitive ribose-5-phosphate isomerase (Rpi) inhibitors 4-deoxy-4-phospho-D-crythronohydroxamic acid, 4-deoxy-4-phospho-D-erythronate, and 4-deoxy-4-phosphonomethyl-D-erythronate, the new hydroxamic acid selectively inhibits Mycobacterium tuberculosis RpiB (K-i = 0.40 mM, K-m/K-i = 4.5) versus Spinacia oleracea RpiA, and hence appears as a promising lead for the design of potent species-specific inhibitors of the bacterial enzyme. © 2005 Elsevier Ltd. All rights reserved

Published in

Tetrahedron Letters
2005, volume: 46, number: 21, pages: 3691-3694

Authors' information

Mowbray, Sherry
Swedish University of Agricultural Sciences, Department of Molecular Biosciences
Roos, Annette K.
Burgos, Emmanuel
Salmon, Laurent

UKÄ Subject classification

Animal and Dairy Science
Food Science
Veterinary Science
Economics and Business
Social Sciences

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