Literature DB >> 19097895

Submicromolar phosphinic inhibitors of Escherichia coli aspartate transcarbamoylase.

Laëtitia Coudray1, Evan R Kantrowitz, Jean-Luc Montchamp.   

Abstract

The design, syntheses, and enzymatic activity of two submicromolar competitive inhibitors of aspartate transcarbamoylase (ATCase) are described. The phosphinate inhibitors are analogs of N-phosphonacetyl-l-aspartate (PALA) but have a reduced charge at the phosphorus moiety. The mechanistic implications are discussed in terms of a possible cyclic transition-state during enzymatic catalysis.

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Year:  2008        PMID： 19097895      PMCID： PMC2743340          DOI： 10.1016/j.bmcl.2008.11.115

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  29 in total

1.  Design, synthesis and activity of bisubstrate, transition-state analogues and competitive inhibitors of aspartate transcarbamylase.

Authors:  Claude Grison; Philippe Coutrot; Corinne Comoy; Laurence Balas; Stéphane Joliez; Guido Lavecchia; Patrick Oliger; Bernadette Penverne; Valérie Serre; Guy Hervé
Journal:  Eur J Med Chem       Date:  2004-04       Impact factor: 6.514

2.  Inhibitor Ionization as a Determinant of Binding to 3-Dehydroquinate Synthase.

Authors:  Feng Tian; Jean-Luc Montchamp; J. W. Frost
Journal:  J Org Chem       Date:  1996-10-18       Impact factor: 4.354

3.  Binding of radiolabeled N-(phosphonacetyl)-L-aspartate to aspartate transcarbamylase from Ehrlich ascites tumor cells.

Authors:  J C White; L H Hines
Journal:  Biochem Pharmacol       Date:  1984-11-15       Impact factor: 5.858

4.  Palladium-catalyzed dehydrative allylation of hypophosphorous acid with allylic alcohols.

Authors:  Karla Bravo-Altamirano; Jean-Luc Montchamp
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

5.  Phosphorus-containing inhibitors of aspartate transcarbamoylase from Escherichia coli.

Authors:  N M Laing; W W Chan; D W Hutchinson; B Oberg
Journal:  FEBS Lett       Date:  1990-01-29       Impact factor: 4.124

6.  T-state active site of aspartate transcarbamylase: crystal structure of the carbamyl phosphate and L-alanosine ligated enzyme.

Authors:  Jingwei Huang; William N Lipscomb
Journal:  Biochemistry       Date:  2006-01-17       Impact factor: 3.162

7.  N-phosphonacetyl-L-isoasparagine a potent and specific inhibitor of Escherichia coli aspartate transcarbamoylase.

Authors:  Joby Eldo; James P Cardia; Elizabeth M O'Day; Jiarong Xia; Hiro Tsuruta; Evan R Kantrowitz
Journal:  J Med Chem       Date:  2006-10-05       Impact factor: 7.446

8.  NiCl2-catalyzed hydrophosphinylation.

Authors:  Patrice Ribière; Karla Bravo-Altamirano; Monika I Antczak; Jennifer D Hawkins; Jean-Luc Montchamp
Journal:  J Org Chem       Date:  2005-05-13       Impact factor: 4.354

9.  Synthesis and biological activity of a series of aspartate transcarbamoylase inhibitors: N-substituted diethyl aspartates and N-substituted-3-oxo-1,4-piperazine-2-acetic acid esters.

Authors:  P L Dutta; W O Foye
Journal:  J Pharm Sci       Date:  1990-05       Impact factor: 3.534

10.  1,1-Bisphosphonate squalene synthase inhibitors: interplay between the isoprenoid subunit and the diphosphate surrogate.

Authors:  D R Magnin; S A Biller; J K Dickson; J V Logan; R M Lawrence; Y Chen; R B Sulsky; C P Ciosek; T W Harrity; K G Jolibois
Journal:  J Med Chem       Date:  1995-07-07       Impact factor: 7.446
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  2 in total

1.  Synthesis and in vitro evaluation of aspartate transcarbamoylase inhibitors.

Authors:  Laëtitia Coudray; Anne F Pennebaker; Jean-Luc Montchamp
Journal:  Bioorg Med Chem       Date:  2009-09-30       Impact factor: 3.641

2.  Temporary Protection of H-Phosphinic Acids as a Synthetic Strategy.

Authors:  Laëtitia Coudray; Jean-Luc Montchamp
Journal:  European J Org Chem       Date:  2009-09
  2 in total

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