Literature DB >> 17165919

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

Freeman M Wong1, Christina C Capule, Weiming Wu.   

Abstract

[Structure: see text] The pKa's of the 6-CH groups of N-methyl-2-pyridone and N-methyl-4-pyridone in aqueous solution were determined. No correlation between the stability of the carbanions and the rate of decarboxylation of the corresponding carboxylic acids was found.

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Year:  2006        PMID： 17165919      PMCID： PMC2743169          DOI： 10.1021/ol0624981

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 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.  Base-catalyzed reactions of 1,3-disubstituted uracils.

Authors:  E G Lovett; D Lipkin
Journal:  J Org Chem       Date:  1977-07-22       Impact factor: 4.354

3.  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

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.  Formation and stability of peptide enolates in aqueous solution.

Authors:  Ana Rios; John P Richard; Tina L Amyes
Journal:  J Am Chem Soc       Date:  2002-07-17       Impact factor: 15.419

9.  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
  9 in total
  12 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.  Polarization in the structures of uracil and thiouracils: Implication for binding with orotidine 5'-monophosphate decarboxylase.

Authors:  Sha Huang; Scott Gronert; Weiming Wu
Journal:  Bioorg Med Chem Lett       Date:  2011-09-01       Impact factor: 2.823

3.  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

4.  Proton transfer from C-6 of uridine 5'-monophosphate catalyzed by orotidine 5'-monophosphate decarboxylase: formation and stability of a vinyl carbanion intermediate and the effect of a 5-fluoro substituent.

Authors:  Wing-Yin Tsang; B McKay Wood; Freeman M Wong; Weiming Wu; John A Gerlt; Tina L Amyes; John P Richard
Journal:  J Am Chem Soc       Date:  2012-08-21       Impact factor: 15.419

5.  Role of a guanidinium cation-phosphodianion pair in stabilizing the vinyl carbanion intermediate of orotidine 5'-phosphate decarboxylase-catalyzed reactions.

Authors:  Bogdana Goryanova; Lawrence M Goldman; Tina L Amyes; John A Gerlt; John P Richard
Journal:  Biochemistry       Date:  2013-10-08       Impact factor: 3.162

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

Authors:  Fong Ying Yeoh; Roxanne R Cuasito; Christina C Capule; Freeman M Wong; Weiming Wu
Journal:  Bioorg Chem       Date:  2007-04-02       Impact factor: 5.275

7.  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

8.  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

9.  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

10.  The stability of aryl carbanions derived from pyridine N-oxide: the role of resonance in stabilizing aryl anions.

Authors:  Scott K Koehn; Ngoc L Tran; Scott Gronert; Weiming Wu
Journal:  J Am Chem Soc       Date:  2010-01-13       Impact factor: 15.419
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