Literature DB >> 18186641

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.

Tina L Amyes1, Bryant M Wood, Kui Chan, John A Gerlt, John P Richard.   

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Year:  2008        PMID: 18186641      PMCID: PMC2652670          DOI: 10.1021/ja710384t

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


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  15 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

Review 4.  Binding energy, specificity, and enzymic catalysis: the circe effect.

Authors:  W P Jencks
Journal:  Adv Enzymol Relat Areas Mol Biol       Date:  1975

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.  Yeast orotidine-5'-phosphate decarboxylase: steady-state and pre-steady-state analysis of the kinetic mechanism of substrate decarboxylation.

Authors:  D J Porter; S A Short
Journal:  Biochemistry       Date:  2000-09-26       Impact factor: 3.162

8.  A proficient enzyme.

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

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.  OMP decarboxylase: an experimental test of electrostatic destabilization of the enzyme-substrate complex.

Authors:  Brian P Callahan; Richard Wolfenden
Journal:  J Am Chem Soc       Date:  2004-11-17       Impact factor: 15.419

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  53 in total

1.  Orotidine 5'-monophosphate decarboxylase: transition state stabilization from remote protein-phosphodianion interactions.

Authors:  Tina L Amyes; Shonoi A Ming; Lawrence M Goldman; B McKay Wood; Bijoy J Desai; John A Gerlt; John P Richard
Journal:  Biochemistry       Date:  2012-05-31       Impact factor: 3.162

2.  Product deuterium isotope effects for orotidine 5'-monophosphate decarboxylase: effect of changing substrate and enzyme structure on the partitioning of the vinyl carbanion reaction intermediate.

Authors:  Krisztina Toth; Tina L Amyes; Bryant M Wood; Kui Chan; John A Gerlt; John P Richard
Journal:  J Am Chem Soc       Date:  2010-05-26       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.  The use of reaction timecourses to determine the level of minor contaminants in enzyme preparations.

Authors:  Lawrence M Goldman; Tina L Amyes
Journal:  Anal Biochem       Date:  2014-01-03       Impact factor: 3.365

5.  Dissecting the total transition state stabilization provided by amino acid side chains at orotidine 5'-monophosphate decarboxylase: a two-part substrate approach.

Authors:  Shonoi A Barnett; Tina L Amyes; Bryant M Wood; John A Gerlt; John P Richard
Journal:  Biochemistry       Date:  2008-07-04       Impact factor: 3.162

Review 6.  Enzyme (re)design: lessons from natural evolution and computation.

Authors:  John A Gerlt; Patricia C Babbitt
Journal:  Curr Opin Chem Biol       Date:  2009-02-23       Impact factor: 8.822

Review 7.  Specificity in transition state binding: the Pauling model revisited.

Authors:  Tina L Amyes; John P Richard
Journal:  Biochemistry       Date:  2013-02-04       Impact factor: 3.162

8.  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

Review 9.  Catalytic efficiency of enzymes: a theoretical analysis.

Authors:  Sharon Hammes-Schiffer
Journal:  Biochemistry       Date:  2012-12-20       Impact factor: 3.162

10.  Activation of R235A mutant orotidine 5'-monophosphate decarboxylase by the guanidinium cation: effective molarity of the cationic side chain of Arg-235.

Authors:  Shonoi A Barnett; Tina L Amyes; B McKay Wood; John A Gerlt; John P Richard
Journal:  Biochemistry       Date:  2010-02-09       Impact factor: 3.162

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