Literature DB >> 21799546

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

Sha Huang1, Freeman M Wong, George T Gassner, Weiming Wu.   

Abstract

α-Halo and α-cyano pyridiniums were found to undergo facile hydrolysis, in contrast to the sluggish reactions of corresponding uracils. The greatly enhanced rates found with pyridinium compounds have indicated a possible source of the rate acceleration seen in the hydrolysis of 6-cyanouridine 5'-monophosphate catalyzed by orotidine 5'-monophosphate decarboxylase.

Entities:  

Year:  2011        PMID： 21799546      PMCID： PMC3143031          DOI： 10.1016/j.tetlet.2011.05.108

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  19 in total

1.  Electrostatic stress in catalysis: structure and mechanism of the enzyme orotidine monophosphate decarboxylase.

Authors:  N Wu; Y Mo; J Gao; E F Pai
Journal:  Proc Natl Acad Sci U S A       Date:  2000-02-29       Impact factor: 11.205

2.  Anatomy of a proficient enzyme: the structure of orotidine 5'-monophosphate decarboxylase in the presence and absence of a potential transition state analog.

Authors:  B G Miller; A M Hassell; R Wolfenden; M V Milburn; S A Short
Journal:  Proc Natl Acad Sci U S A       Date:  2000-02-29       Impact factor: 11.205

3.  The crystal structure and mechanism of orotidine 5'-monophosphate decarboxylase.

Authors:  T C Appleby; C Kinsland; T P Begley; S E Ealick
Journal:  Proc Natl Acad Sci U S A       Date:  2000-02-29       Impact factor: 11.205

4.  Crystal structures of inhibitor complexes reveal an alternate binding mode in orotidine-5'-monophosphate decarboxylase.

Authors:  Ning Wu; Emil F Pai
Journal:  J Biol Chem       Date:  2002-05-13       Impact factor: 5.157

5.  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

6.  Product deuterium isotope effect for orotidine 5'-monophosphate decarboxylase: evidence for the existence of a short-lived carbanion intermediate.

Authors:  Krisztina Toth; Tina L Amyes; Bryant M Wood; Kui Chan; John A Gerlt; John P Richard
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

7.  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

8.  Remarkable rate enhancement of orotidine 5'-monophosphate decarboxylase is due to transition-state stabilization rather than to ground-state destabilization.

Authors:  A Warshel; M Strajbl; J Villà; J Florián
Journal:  Biochemistry       Date:  2000-12-05       Impact factor: 3.162

9.  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

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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  5 in total

1.  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

2.  The element effect revisited: factors determining leaving group ability in activated nucleophilic aromatic substitution reactions.

Authors:  Nicholas A Senger; Bo Bo; Qian Cheng; James R Keeffe; Scott Gronert; Weiming Wu
Journal:  J Org Chem       Date:  2012-10-17       Impact factor: 4.354

3.  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

4.  Hydrolysis of α-chloro-substituted 2- and 4-pyridones: rate enhancement by zwitterionic structure.

Authors:  Ronald C Tan; Janie Q T Vien; Weiming Wu
Journal:  Bioorg Med Chem Lett       Date:  2011-12-03       Impact factor: 2.823

5.  Reactivity in the nucleophilic aromatic substitution reactions of pyridinium ions.

Authors:  Jeannette T Bowler; Freeman M Wong; Scott Gronert; James R Keeffe; Weiming Wu
Journal:  Org Biomol Chem       Date:  2014-08-28       Impact factor: 3.876
  5 in total

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