Literature DB >> 17400276

Carbanions from decarboxylation of orotate analogs: stability and mechanistic implications.

Fong Ying Yeoh1, Roxanne R Cuasito, Christina C Capule, Freeman M Wong, Weiming Wu.   

Abstract

The pKa's of the 6-CH groups of 1,3-dimethyluracil, N-methyl-2-pyridone, and N-methyl-4-pyridone were determined through their reactions with bases derived from carbon acids with known pKa and the reactions of their corresponding carbanions with the carbon acids. No correlation between the stability of the carbanions and the rate of decarboxylation of corresponding carboxylic acids was found.

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Year:  2007        PMID： 17400276      PMCID： PMC2757000          DOI： 10.1016/j.bioorg.2007.02.001

Source DB:  PubMed          Journal:  Bioorg Chem        ISSN： 0045-2068            Impact factor:   5.275


  8 in total

1.  The mechanism of orotidine 5'-monophosphate decarboxylase: catalysis by destabilization of the substrate.

Authors:  W Y Feng; T J Austin; F Chew; S Gronert; W Wu
Journal:  Biochemistry       Date:  2000-02-22       Impact factor: 3.162

2.  Modest catalysis of the decarboxylation of orotate by hydrogen bonding: a theoretical model for orotidine- 5' -monophosphate decarboxylase.

Authors:  Diana L Shem; Scott Gronert; Weiming Wu
Journal:  Bioorg Chem       Date:  2004-04       Impact factor: 5.275

3.  Stability of the 6-carbanion of uracil analogues: mechanistic implications for model reactions of orotidine-5'-monophosphate decarboxylase.

Authors:  Freeman M Wong; Christina C Capule; Weiming Wu
Journal:  Org Lett       Date:  2006-12-21       Impact factor: 6.005

4.  Accelerated decarboxylation of 1,3-dimethylorotic acid in ionic liquid.

Authors:  Freeman M Wong; Weiming Wu
Journal:  Bioorg Chem       Date:  2006-02-24       Impact factor: 5.275

5.  Mechanism of decarboxylation of 1,3-dimethylorotic acid. A model for orotidine 5'-phosphate decarboxylase.

Authors:  P Beak; B Siegel
Journal:  J Am Chem Soc       Date:  1976-06-09       Impact factor: 15.419

6.  A proficient enzyme revisited: the predicted mechanism for orotidine monophosphate decarboxylase.

Authors:  J K Lee; K N Houk
Journal:  Science       Date:  1997-05-09       Impact factor: 47.728

7.  A proficient enzyme.

Authors:  A Radzicka; R Wolfenden
Journal:  Science       Date:  1995-01-06       Impact factor: 47.728

8.  Equilibrium of formation of the 6-carbanion of UMP, a potential intermediate in the action of OMP decarboxylase.

Authors:  Annette Sievers; Richard Wolfenden
Journal:  J Am Chem Soc       Date:  2002-11-27       Impact factor: 15.419
  8 in total
  10 in total

1.  Convenient synthesis of N1-substituted orotic acid derivatives.

Authors:  Jeannette T Bowler; Caitlin R Clausen; Daniel J Blackburn; Weiming Wu
Journal:  Tetrahedron Lett       Date:  2014-11-19       Impact factor: 2.415

2.  Formation and stability of a vinyl carbanion at the active site of orotidine 5'-monophosphate decarboxylase: pKa of the C-6 proton of enzyme-bound UMP.

Authors:  Tina L Amyes; Bryant M Wood; Kui Chan; John A Gerlt; John P Richard
Journal:  J Am Chem Soc       Date:  2008-01-11       Impact factor: 15.419

3.  Mechanism of the orotidine 5'-monophosphate decarboxylase-catalyzed reaction: evidence for substrate destabilization.

Authors:  Kui K Chan; B McKay Wood; Alexander A Fedorov; Elena V Fedorov; Heidi J Imker; Tina L Amyes; John P Richard; Steven C Almo; John A Gerlt
Journal:  Biochemistry       Date:  2009-06-23       Impact factor: 3.162

4.  Substrate distortion contributes to the catalysis of orotidine 5'-monophosphate decarboxylase.

Authors:  Masahiro Fujihashi; Toyokazu Ishida; Shingo Kuroda; Lakshmi P Kotra; Emil F Pai; Kunio Miki
Journal:  J Am Chem Soc       Date:  2013-11-11       Impact factor: 15.419

5.  Stabilities of Uracil and Pyridone-Based Carbanions: A Systematic Study in the Gas Phase and Solution and Implications for the Mechanism of Orotidine-5'-Monophosphate Decarboxylase.

Authors:  Nicholas A Senger; Carly E Bliss; James R Keeffe; Scott Gronert; Weiming Wu
Journal:  Tetrahedron       Date:  2013-07-01       Impact factor: 2.457

6.  Accelerated hydrolysis of α-halo and α-cyano pyridinium relative to uracil derivatives: a model for ODCase-catalyzed hydrolysis of 6-cyanoUMP.

Authors:  Sha Huang; Freeman M Wong; George T Gassner; Weiming Wu
Journal:  Tetrahedron Lett       Date:  2011-08-03       Impact factor: 2.415

7.  Catalysis in Enzymatic Decarboxylations: Comparison of Selected Cofactor-dependent and Cofactor-independent Examples.

Authors:  Frank Jordan; Hetalben Patel
Journal:  ACS Catal       Date:  2013-07-05       Impact factor: 13.084

8.  Enzymatic Catalysis of Proton Transfer and Decarboxylation Reactions.

Authors:  John P Richard
Journal:  Pure Appl Chem       Date:  2011-07-08       Impact factor: 2.453

9.  Orotic acid decarboxylation in water and nonpolar solvents: a potential role for desolvation in the action of OMP decarboxylase.

Authors:  Charles A Lewis; Richard Wolfenden
Journal:  Biochemistry       Date:  2009-09-15       Impact factor: 3.162

10.  Improved synthesis of N1-substituted orotic acid derivatives.

Authors:  Nicholas A Senger; Jeannette T Bowler; Rene S Mercado; Sidney Lin; Weiming Wu
Journal:  Tetrahedron Lett       Date:  2013-08-07       Impact factor: 2.415
  10 in total

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