Literature DB >> 20448876

The hydrolysis of phosphate diesters in cyclohexane and acetone.

Randy B Stockbridge1, Richard Wolfenden.   

Abstract

The hydrolysis of phosphate diesters is one of the most difficult reactions known. Here we show that in acetone or cyclohexane, at 25 degrees C, phosphodiesters undergo hydrolysis 5 x 10(5) and 2 x 10(9)-fold more rapidly than in water, respectively, and that this rate enhancement is achieved by lowering the enthalpy of activation.

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Year:  2010        PMID： 20448876      PMCID： PMC2904243          DOI： 10.1039/c0cc00229a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  9 in total

1.  Mechanisms of thiamine-catalyzed reactions. Decarboxylation of 2-(1-carboxy-1-hydroxyethyl)-3,4-dimethylthiazolium chloride.

Authors:  J Crosby; R Stone; G E Lienhard
Journal:  J Am Chem Soc       Date:  1970-05-06       Impact factor: 15.419

2.  Determination of amines and quaternary ammonium ions as complexes with picrate. 3. Relations between extraction constants and the nature of the cation and of the organic phase.

Authors:  K Gustavii
Journal:  Acta Pharm Suec       Date:  1967-09

3.  Phosphate monoester hydrolysis in cyclohexane.

Authors:  Randy B Stockbridge; Richard Wolfenden
Journal:  J Am Chem Soc       Date:  2009-12-30       Impact factor: 15.419

4.  Mapping the transition state for ATP hydrolysis: implications for enzymatic catalysis.

Authors:  S J Admiraal; D Herschlag
Journal:  Chem Biol       Date:  1995-11

5.  Active Site of alpha-Chymotrypsin Activation by Association-Desolvation.

Authors:  S G Cohen; V M Vaidya; R M Schultz
Journal:  Proc Natl Acad Sci U S A       Date:  1970-06       Impact factor: 11.205

6.  Solvent effects and alkali metal ion catalysis in phosphodiester hydrolysis.

Authors:  Paola Gomez-Tagle; Idania Vargas-Zúñiga; Olga Taran; Anatoly K Yatsimirsky
Journal:  J Org Chem       Date:  2006-12-22       Impact factor: 4.354

7.  The time required for water attack at the phosphorus atom of simple phosphodiesters and of DNA.

Authors:  Gottfried K Schroeder; Chetan Lad; Paul Wyman; Nicholas H Williams; Richard Wolfenden
Journal:  Proc Natl Acad Sci U S A       Date:  2006-03-06       Impact factor: 11.205

8.  The rate of hydrolysis of phosphomonoester dianions and the exceptional catalytic proficiencies of protein and inositol phosphatases.

Authors:  Chetan Lad; Nicholas H Williams; Richard Wolfenden
Journal:  Proc Natl Acad Sci U S A       Date:  2003-04-29       Impact factor: 11.205

9.  Dineopentyl phosphate hydrolysis: evidence for stepwise water attack.

Authors:  Shina C L Kamerlin; Nicholas H Williams; Arieh Warshel
Journal:  J Org Chem       Date:  2008-08-27       Impact factor: 4.354
  9 in total
  2 in total

Review 1.  Massive thermal acceleration of the emergence of primordial chemistry, the incidence of spontaneous mutation, and the evolution of enzymes.

Authors:  Richard Wolfenden
Journal:  J Biol Chem       Date:  2014-09-10       Impact factor: 5.157

2.  Enhancement of the rate of pyrophosphate hydrolysis by nonenzymatic catalysts and by inorganic pyrophosphatase.

Authors:  Randy B Stockbridge; Richard Wolfenden
Journal:  J Biol Chem       Date:  2011-04-01       Impact factor: 5.157
  2 in total

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