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

Emmanuel Burgos; Annette K. Roos; Sherry L. Mowbray; Laurent Salmon

doi:10.1016/j.tetlet.2005.03.151

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

Emmanuel Burgos
, Annette K. Roos
, Sherry L. Mowbray
, Laurent Salmon

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

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-erythronohydroxamic 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.

Original language	English (US)
Pages (from-to)	3691-3694
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	21
DOIs	https://doi.org/10.1016/j.tetlet.2005.03.151
State	Published - May 23 2005
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

5-Phosphate D-ribose isomerase
6-Phosphate D-allose isomerase
Competitive inhibitor
Phosphate sugar
RpiB

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.03.151

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@article{5852f4c960ff4868a028c2ff187835c3,

title = "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",

abstract = "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-erythronohydroxamic acid, 4-deoxy-4-phospho-d-erythronate, and 4-deoxy-4-phosphonomethyl-d-erythronate, the new hydroxamic acid selectively inhibits Mycobacterium tuberculosis RpiB (Ki = 0.40 mM, Km/Ki = 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.",

keywords = "5-Phosphate D-ribose isomerase, 6-Phosphate D-allose isomerase, Competitive inhibitor, Phosphate sugar, RpiB",

author = "Emmanuel Burgos and Roos, \{Annette K.\} and Mowbray, \{Sherry L.\} and Laurent Salmon",

note = "Funding Information: Financial support from The Minist{\`e}re de l{\textquoteright}Education Nationale et de la Recherche (E. B., 2001-2004), the Swedish Research Council (VR) and the Swedish Foundation for Strategic Research (SSF) are gratefully acknowledged.",

year = "2005",

month = may,

day = "23",

doi = "10.1016/j.tetlet.2005.03.151",

language = "English (US)",

volume = "46",

pages = "3691--3694",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "21",

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TY - JOUR

T1 - Synthesis of 5-deoxy-5-phospho-D-ribonohydroxamic acid

T2 - A new competitive and selective inhibitor of type B ribose-5-phosphate isomerase from Mycobacterium tuberculosis

AU - Burgos, Emmanuel

AU - Roos, Annette K.

AU - Mowbray, Sherry L.

AU - Salmon, Laurent

N1 - Funding Information: Financial support from The Ministère de l’Education Nationale et de la Recherche (E. B., 2001-2004), the Swedish Research Council (VR) and the Swedish Foundation for Strategic Research (SSF) are gratefully acknowledged.

PY - 2005/5/23

Y1 - 2005/5/23

N2 - 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-erythronohydroxamic acid, 4-deoxy-4-phospho-d-erythronate, and 4-deoxy-4-phosphonomethyl-d-erythronate, the new hydroxamic acid selectively inhibits Mycobacterium tuberculosis RpiB (Ki = 0.40 mM, Km/Ki = 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.

AB - 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-erythronohydroxamic acid, 4-deoxy-4-phospho-d-erythronate, and 4-deoxy-4-phosphonomethyl-d-erythronate, the new hydroxamic acid selectively inhibits Mycobacterium tuberculosis RpiB (Ki = 0.40 mM, Km/Ki = 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.

KW - 5-Phosphate D-ribose isomerase

KW - 6-Phosphate D-allose isomerase

KW - Competitive inhibitor

KW - Phosphate sugar

KW - RpiB

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DO - 10.1016/j.tetlet.2005.03.151

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

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

Abstract

UN SDGs

Keywords

ASJC Scopus subject areas

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