Covalent catalysis by pyridoxal: evaluation of the effect of the cofactor on the carbon acidity of glycine (Q37074136)

18 August 2017

Covalent catalysis by pyridoxal: evaluation of the effect of the cofactor on the carbon acidity of glycine (English)

1 reference

18 August 2017

John P Richard

2

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author name string

Krisztina Toth

series ordinal

1

1 reference

PMC publication ID

2631443

18 August 2017

language of work or name

English

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publication date

14 February 2007

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18 August 2017

9

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Journal of the American Chemical Society

inferred from page(s)

published in

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18 August 2017

129

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18 August 2017

10

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18 August 2017

3013-3021

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Claisen-type addition of glycine to a pyridoxal iminium ion in water

18 August 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Transition state stabilization and alpha-amino carbon acidity in alanine racemase.

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Structural insights into stereochemical inversion by diaminopimelate epimerase: an antibacterial drug target

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Crystal structure, catalytic mechanism, and mitogenic properties of Trypanosoma cruzi proline racemase

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Reaction specificity in pyridoxal phosphate enzymes

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

On the importance of being zwitterionic: enzymatic catalysis of decarboxylation and deprotonation of cationic carbon

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Pyridoxal phosphate enzymes: mechanistic, structural, and evolutionary considerations

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Formation and stability of peptide enolates in aqueous solution.

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

From cofactor to enzymes. The molecular evolution of pyridoxal-5'-phosphate-dependent enzymes

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Determination of the structure of alanine racemase from Bacillus stearothermophilus at 1.9-A resolution

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Dialkylglycine decarboxylase structure: bifunctional active site and alkali metal sites

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

The structural basis for the altered substrate specificity of the R292D active site mutant of aspartate aminotransferase from E. coli

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Reaction pathways and mechanisms of pyridoxal catalysis.

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Mechanism of action of aspartate aminotransferase proposed on the basis of its spatial structure

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Catalytic Aspects of Enzymatic Racemization

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

On the ionization state of the substrate in the active site of glutamate racemase. A QM/MM study about the importance of being zwitterionic.

29 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Hydrophobic and electronic factors in the design of dialkylglycine decarboxylase mimics

4 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Carbon acidity of the alpha-pyridinium carbon of a pyridoxamine analog.

4 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Claisen-type addition of glycine to pyridoxal in water.

4 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Alanine racemase free energy profiles from global analyses of progress curves

4 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Formation and stability of the enolates of N-protonated proline methyl ester and proline zwitterion in aqueous solution: a nonenzymatic model for the first step in the racemization of proline catalyzed by proline racemase

4 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Multiple Hydrogen Kinetic Isotope Effects for Enzymes Catalyzing Exchange with Solvent: Application to Alanine Racemase

4 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Formation and stability of enolates of acetamide and acetate anion: an Eigen plot for proton transfer at alpha-carbonyl carbon

4 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Glycine enolates: the large effect of iminium ion formation on alpha-amino carbon acidity

4 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Lysine 258 in aspartate aminotransferase: enforcer of the Circe effect for amino acid substrates and general-base catalyst for the 1,3-prototropic shift.

4 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Comparison of the rate constants for general base catatlyzed prototropy and racemization of the aldimine species formed from 3-hydroxypyridine-4-carboxaldehyde and alanine

4 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2631443

Aminomalonic acid. Spontaneous decarboxylation and reaction with 5-deoxypyridoxal

4 September 2018

1 reference

12 December 2020

Spectroscopic studies of quinonoid species from pyridoxal 5'-phosphate

1 reference

12 December 2020

Evidence for a two-base mechanism involving tyrosine-265 from arginine-219 mutants of alanine racemase

1 reference

12 December 2020

Role of tyrosine 265 of alanine racemase from Bacillus stearothermophilus

1 reference

12 December 2020

Tyrosine 265 of alanine racemase serves as a base abstracting alpha-hydrogen from L-alanine: the counterpart residue to lysine 39 specific to D-alanine

1 reference

12 December 2020

Identifiers

DOI

10.1021/JA0679228

1 reference

18 August 2017

1 reference

PMC publication ID

2631443

18 August 2017

PubMed publication ID

17298067

1 reference

PMC publication ID

2631443