Literature DB >> 19305514

ENANTIOMERIC SYNTHESIS OF 2-C-METHYL-D-ERYTHRITOL 2, 4-CYCLODIPHOSPHATE.

Prabagaran Narayanasamy1, Dean C Crick.   

Abstract

Enantiomerically pure 2-C-methyl-D-erythritol 2,4-cyclodiphosphate 1 (ME-CPP) is synthesized from 1,2-O-isopropylidene-α-D-xylofuranose with facile phosphorylation in good yield. Subsequently, the synthesized enantiomerically pure 1 can be used as a substrate in IspG assays to identify inhibitors that may be developed into antibacterial drug leads.

Entities:  

Year:  2008        PMID： 19305514      PMCID： PMC2658599          DOI： 10.3987/com-08-s(n)72

Source DB:  PubMed          Journal:  Heterocycles        ISSN： 0385-5414            Impact factor:   0.831


  8 in total

Review 1.  The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants.

Authors:  M Rohmer
Journal:  Nat Prod Rep       Date:  1999-10       Impact factor: 13.423

2.  Synthesis of 2-C-methyl-D-erythritol 2,4-cyclopyrophosphate.

Authors:  José-Luis Giner; William V Ferris
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

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

4.  Cloning and expression of IspDF from Mesorhizobium loti. Characterization of a bifunctional protein that catalyzes non-consecutive steps in the methylerythritol phosphate pathway.

Authors:  Charles A Testa; Christian Lherbet; Florence Pojer; Joseph P Noel; C Dale Poulter
Journal:  Biochim Biophys Acta       Date:  2005-08-31

5.  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

6.  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

7.  Synthesis of enantiopure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate from D-arabitol.

Authors:  Marek Urbansky; Chad E Davis; Jacob D Surjan; Robert M Coates
Journal:  Org Lett       Date:  2004-01-08       Impact factor: 6.005

Review 8.  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
  8 in total
  4 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.  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

4.  Synthesis of lamellarin R, lukianol A, lamellarin O and their analogues.

Authors:  Iddum Satyanarayana; Ding-Yah Yang; Teau-Jiuan Liou
Journal:  RSC Adv       Date:  2020-11-27       Impact factor: 4.036
  4 in total

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