Literature DB >> 19088853

Chemoenzymatic synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol: A substrate for IspE.

Prabagaran Narayanasamy1, Hyungjin Eoh, Dean C Crick.   

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.

Entities:  

Year:  2008        PMID： 19088853      PMCID： PMC2832204          DOI： 10.1016/j.tetlet.2008.05.074

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  12 in total

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3.  1-Deoxy-D-xylulose 5-phosphate reductoisomerase (IspC) from Mycobacterium tuberculosis: towards understanding mycobacterial resistance to fosmidomycin.

Authors:  Rakesh K Dhiman; Merrill L Schaeffer; Ann Marie Bailey; Charles A Testa; Hataichanok Scherman; Dean C Crick
Journal:  J Bacteriol       Date:  2005-12       Impact factor: 3.490

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Authors:  Victoria Clay Wright; Jeani Chang; Gary Jeng; Maurizio Macaluso
Journal:  MMWR Surveill Summ       Date:  2006-05-26

5.  Synthesis of 2-C-methyl-D-erythritol 4-phosphate: the first pathway-specific intermediate in the methylerythritol phosphate route to isoprenoids.

Authors:  A T Koppisch; B S Blagg; C D Poulter
Journal:  Org Lett       Date:  2000-01-27       Impact factor: 6.005

6.  Synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol and 2-C-methyl-D-erythritol-4-phosphate.

Authors:  Andrew T Koppisch; C Dale Poulter
Journal:  J Org Chem       Date:  2002-07-26       Impact factor: 4.354

7.  An intramolecular Diels-Alder approach to the eunicelins: enantioselective total synthesis of ophirin B.

Authors:  Michael T Crimmins; Brandon H Brown
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8.  Characterization of the Mycobacterium tuberculosis 4-diphosphocytidyl-2-C-methyl-D-erythritol synthase: potential for drug development.

Authors:  Hyungjin Eoh; Amanda C Brown; Lori Buetow; William N Hunter; Tanya Parish; Devinder Kaur; Patrick J Brennan; Dean C Crick
Journal:  J Bacteriol       Date:  2007-10-05       Impact factor: 3.490

9.  Identification, cloning, purification, and enzymatic characterization of Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate synthase.

Authors:  Ann Marie Bailey; Sebabrata Mahapatra; Patrick J Brennan; Dean C Crick
Journal:  Glycobiology       Date:  2002-12       Impact factor: 4.313

Review 10.  The cell-wall core of Mycobacterium tuberculosis in the context of drug discovery.

Authors:  Patrick J Brennan; Dean C Crick
Journal:  Curr Top Med Chem       Date:  2007       Impact factor: 3.295
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  9 in total

1.  Synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate and kinetic studies of Mycobacterium tuberculosis IspF.

Authors:  Prabagaran Narayanasamy; Hyungjin Eoh; Patrick J Brennan; Dean C Crick
Journal:  Chem Biol       Date:  2010-02-26

2.  Synthesis of chirally pure 1-deoxy-d-xylulose-5-phosphate : A substrate for IspC assay to determine M. tb inhibitor.

Authors:  Benson J Edagwa; Prabagaran Narayanasamy
Journal:  Chem Sci J       Date:  2013-12-30

3.  Genetics of Capsular Polysaccharides and Cell Envelope (Glyco)lipids.

Authors:  Mamadou Daffé; Dean C Crick; Mary Jackson
Journal:  Microbiol Spectr       Date:  2014

4.  Formal Synthesis of 4-diphosphocytidyl-2-C-methyl D-erythritol From D-(+)-Arabitol.

Authors:  Sina I Odejinmi; Rafael G Rascon; Wyman Chen; Kent Lai
Journal:  Tetrahedron       Date:  2012-10-28       Impact factor: 2.457

5.  2C-Methyl-d-erythritol 4-phosphate enhances and sustains cyclodiphosphate synthase IspF activity.

Authors:  J Kipchirchir Bitok; Caren Freel Meyers
Journal:  ACS Chem Biol       Date:  2012-08-06       Impact factor: 5.100

6.  Expression and characterization of soluble 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase from bacterial pathogens.

Authors:  Hyungjin Eoh; Prabagaran Narayanasamy; Amanda C Brown; Tanya Parish; Patrick J Brennan; Dean C Crick
Journal:  Chem Biol       Date:  2009-12-24

7.  Synthesis and evaluation of stable substrate analogs as potential modulators of cyclodiphosphate synthase IspF.

Authors:  J Kipchirchir Bitok; Caren Freel Meyers
Journal:  Medchemcomm       Date:  2013-01       Impact factor: 3.597

8.  Gallium nanoparticles facilitate phagosome maturation and inhibit growth of virulent Mycobacterium tuberculosis in macrophages.

Authors:  Seoung-Ryoung Choi; Bradley E Britigan; David M Moran; Prabagaran Narayanasamy
Journal:  PLoS One       Date:  2017-05-18       Impact factor: 3.240

9.  Synthetic Routes to Methylerythritol Phosphate Pathway Intermediates and Downstream Isoprenoids.

Authors:  Sarah K Jarchow-Choy; Andrew T Koppisch; David T Fox
Journal:  Curr Org Chem       Date:  2014-04       Impact factor: 2.180
  9 in total

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