Literature DB >> 24860687

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

Benson J Edagwa1, Prabagaran Narayanasamy1.   

Abstract

1-Deoxy-D-xylulsose-5-phosphate (DXP) is a key intermediate in the non-mevalonate or methyl erythritol phosphate (MEP) pathway for the biosynthesis of isoprenoid, which are essential building blocks involved in the construction of pathogens growth. Since the homologous enzymes of this pathway are not present in vertebrates, including humans, the MEP pathway presents a viable source for antimicrobial drug targets. However, an insight into the features of the enzymes involved in this pathway has been plagued by lack of chirally pure substrates. Here in, we report an efficient synthesis of enantiomerically pure 1-deoxy-D-xylulose-5-phosphate from commercially available 1,2-O-isopropylidene-α-D-xylofuranose through Weinreb amide formation in shorter route.

Entities:  

Year:  2013        PMID: 24860687      PMCID: PMC4032121     

Source DB:  PubMed          Journal:  Chem Sci J        ISSN: 2150-3494


  11 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.  Mechanism of acylation of lithium phenylacetylide with a Weinreb amide.

Authors:  Bo Qu; David B Collum
Journal:  J Org Chem       Date:  2006-09-01       Impact factor: 4.354

3.  Inhibition Studies on Enzymes Involved in Isoprenoid Biosynthesis: Focus on Two Potential Drug Targets: DXR and IDI-2 Enzymes.

Authors:  Jérôme de Ruyck; Johan Wouters; C Dale Poulter
Journal:  Curr Enzym Inhib       Date:  2011-07

4.  Modifications around the hydroxamic acid chelating group of fosmidomycin, an inhibitor of the metalloenzyme 1-deoxyxylulose 5-phosphate reductoisomerase (DXR).

Authors:  Catherine Zinglé; Lionel Kuntz; Denis Tritsch; Catherine Grosdemange-Billiard; Michel Rohmer
Journal:  Bioorg Med Chem Lett       Date:  2012-09-15       Impact factor: 2.823

5.  Isoprenoid biosynthesis via the MEP pathway. Synthesis of (3,4)-3,4-dihydroxy-5-oxohexylphosphonic acid, an isosteric analogue of 1-deoxy-D-xylulose 5-phosphate, the substrate of the 1-deoxy-D-xylulose 5-phosphate reducto-isomerase.

Authors:  Odile Meyer; Catherine Grosdemange-Billiard; Denis Tritsch; Michel Rohmer
Journal:  Org Biomol Chem       Date:  2003-11-06       Impact factor: 3.876

Review 6.  Isoprenoids: remarkable diversity of form and function.

Authors:  Sarah A Holstein; Raymond J Hohl
Journal:  Lipids       Date:  2004-04       Impact factor: 1.880

7.  Isoprenoid biosynthesis via the MEP pathway: in vivo Mössbauer spectroscopy identifies a [4Fe-4S]2+ center with unusual coordination sphere in the LytB protein.

Authors:  Myriam Seemann; Karnjapan Janthawornpong; Julia Schweizer; Lars H Böttger; Adam Janoschka; Anne Ahrens-Botzong; Erasmienne Ngouamegne Tambou; Olaf Rotthaus; Alfred X Trautwein; Michel Rohmer
Journal:  J Am Chem Soc       Date:  2009-09-23       Impact factor: 15.419

8.  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

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

Authors:  Prabagaran Narayanasamy; Dean C Crick
Journal:  Heterocycles       Date:  2008-03-30       Impact factor: 0.831

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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