Chemoenzymatic synthesis of 4-diphosphocytidyl-2-C-methyl-d-erythritol: a substrate for IspE

Prabagaran Narayanasamy; Hyungjin Eoh; Dean C. Crick

doi:10.1016/j.tetlet.2008.05.074

Chemoenzymatic synthesis of 4-diphosphocytidyl-2-C-methyl-d-erythritol: a substrate for IspE

Prabagaran Narayanasamy, Hyungjin Eoh, Dean C. Crick

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

14 Scopus citations

Abstract

Enantiomerically pure 2-C-methyl-d-erythritol 4-phosphate 1 (MEP) is synthesized from 1,2-O-isopropylidene-α-d-xylofuranose via facile benzylation in good yield. Subsequently, 1 is used for enzymatic synthesis of 4-diphosphocytidyl-2-C-methyl-d-erythritol 2 (CDP-ME) using 4-diphosphocytidyl-2-C-methyl-d-erythritol synthase (IspD). The chemoenzymatically synthesized 2 can be used as substrate for assay of IspE and for high throughput screening to identify IspE inhibitors.

Original language	English (US)
Pages (from-to)	4461-4463
Number of pages	3
Journal	Tetrahedron Letters
Volume	49
Issue number	29-30
DOIs	https://doi.org/10.1016/j.tetlet.2008.05.074
State	Published - Jul 21 2008
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Chemoenzymatic synthesis of 4-diphosphocytidyl-2-C-methyl-d-erythritol: a substrate for IspE",

abstract = "Enantiomerically pure 2-C-methyl-d-erythritol 4-phosphate 1 (MEP) is synthesized from 1,2-O-isopropylidene-α-d-xylofuranose via facile benzylation in good yield. Subsequently, 1 is used for enzymatic synthesis of 4-diphosphocytidyl-2-C-methyl-d-erythritol 2 (CDP-ME) using 4-diphosphocytidyl-2-C-methyl-d-erythritol synthase (IspD). The chemoenzymatically synthesized 2 can be used as substrate for assay of IspE and for high throughput screening to identify IspE inhibitors.",

author = "Prabagaran Narayanasamy and Hyungjin Eoh and Crick, {Dean C.}",

note = "Funding Information: This research was supported by NIH/NIAID Grant No. AI65357-030010. ",

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T1 - Chemoenzymatic synthesis of 4-diphosphocytidyl-2-C-methyl-d-erythritol

T2 - a substrate for IspE

AU - Narayanasamy, Prabagaran

AU - Eoh, Hyungjin

AU - Crick, Dean C.

N1 - Funding Information: This research was supported by NIH/NIAID Grant No. AI65357-030010.

PY - 2008/7/21

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AB - Enantiomerically pure 2-C-methyl-d-erythritol 4-phosphate 1 (MEP) is synthesized from 1,2-O-isopropylidene-α-d-xylofuranose via facile benzylation in good yield. Subsequently, 1 is used for enzymatic synthesis of 4-diphosphocytidyl-2-C-methyl-d-erythritol 2 (CDP-ME) using 4-diphosphocytidyl-2-C-methyl-d-erythritol synthase (IspD). The chemoenzymatically synthesized 2 can be used as substrate for assay of IspE and for high throughput screening to identify IspE inhibitors.

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Chemoenzymatic synthesis of 4-diphosphocytidyl-2-C-methyl-d-erythritol: a substrate for IspE

Abstract

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