Literature DB >> 23049145

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

Sina I Odejinmi1, Rafael G Rascon, Wyman Chen, Kent Lai.   

Abstract

2-C-methyl-D-erythritol-4-phosphate (MEP) is a key chemical intermediate of the non-mevalonate pathway for isoprenoid biosynthesis employed by many pathogenic microbes. MEP is also the precursor for the synthesis of 4-diphosphocytidyl-2-C-methyl D-erythritol (CDP-ME), another key intermediate of the non-mevalonate pathway. As this pathway is non-existent in higher animals, including humans, it represents great opportunities for novel antimicrobial development. To facilitate the in-depth studies of this pathway, we reported here a formal synthesis of CDP-ME through a new synthesis of 2-C-Methyl-D-erythritol-4-phosphoric acid from D-(+)-arabitol.

Entities:  

Year:  2012        PMID: 23049145      PMCID: PMC3462025          DOI: 10.1016/j.tet.2012.08.020

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  44 in total

1.  An efficient preparation of 2-C-methyl-D-erythritol 4-phosphoric acid and its derivatives

Authors: 
Journal:  J Org Chem       Date:  2000-01-28       Impact factor: 4.354

2.  Biosynthesis of isoprenoids: crystal structure of 4-diphosphocytidyl-2C-methyl-D-erythritol kinase.

Authors:  Linda Miallau; Magnus S Alphey; Lauris E Kemp; Gordon A Leonard; Sean M McSweeney; Stefan Hecht; Adelbert Bacher; Wolfgang Eisenreich; Felix Rohdich; William N Hunter
Journal:  Proc Natl Acad Sci U S A       Date:  2003-07-23       Impact factor: 11.205

Review 3.  The non-mevalonate pathway of isoprenoid precursor biosynthesis.

Authors:  William N Hunter
Journal:  J Biol Chem       Date:  2007-04-18       Impact factor: 5.157

Review 4.  Regulation of the mevalonate pathway.

Authors:  J L Goldstein; M S Brown
Journal:  Nature       Date:  1990-02-01       Impact factor: 49.962

Review 5.  [Non-mevalonate pathway. A new pathway for the biosynthesis of isopentenyl diphosphate].

Authors:  H Seto
Journal:  Tanpakushitsu Kakusan Koso       Date:  1997-12

6.  Functional evidence for the involvement of Arabidopsis IspF homolog in the nonmevalonate pathway of plastid isoprenoid biosynthesis.

Authors:  Ming-Hsiun Hsieh; Howard M Goodman
Journal:  Planta       Date:  2005-10-18       Impact factor: 4.116

Review 7.  An overview of the non-mevalonate pathway for terpenoid biosynthesis in plants.

Authors:  Vinod Shanker Dubey; Ritu Bhalla; Rajesh Luthra
Journal:  J Biosci       Date:  2003-09       Impact factor: 1.826

8.  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

9.  Kinetic analysis of Escherichia coli 2-C-methyl-D-erythritol-4-phosphate cytidyltransferase, wild type and mutants, reveals roles of active site amino acids.

Authors:  Stéphane B Richard; Antonietta M Lillo; Charles N Tetzlaff; Marianne E Bowman; Joseph P Noel; David E Cane
Journal:  Biochemistry       Date:  2004-09-28       Impact factor: 3.162

Review 10.  Suppression of mevalonate pathway activities by dietary isoprenoids: protective roles in cancer and cardiovascular disease.

Authors:  C E Elson
Journal:  J Nutr       Date:  1995-06       Impact factor: 4.798

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  1 in total

1.  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

  1 in total

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