Literature DB >> 20097067

Chemoenzymatic synthesis of 1-deaza-pyridoxal 5'-phosphate.

Wait R Griswold1, Michael D Toney.   

Abstract

The first synthesis of 1-deaza-pyridoxal 5'-phosphate (2-formyl-3-hydroxy-4-methylbenzyl phosphate) is described. The chemoenzymatic approach described here is a reliable route to this important isosteric pyridoxal phosphate analogue. This work enables elucidation of the role of the pyridine nitrogen in pyridoxal 5'-phosphate dependent enzymes. Copyright 2010 Elsevier Ltd. All rights reserved.

Entities:  

Mesh:

Substances:

Year:  2010        PMID: 20097067      PMCID: PMC3357107          DOI: 10.1016/j.bmcl.2010.01.002

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  15 in total

1.  Catalytic racemization of amino acids by pyridoxal and metal salts.

Authors:  J OLIVARD; D E METZLER; E E SNELL
Journal:  J Biol Chem       Date:  1952-12       Impact factor: 5.157

Review 2.  Pyridoxal enzymes: mechanistic diversity and uniformity.

Authors:  H Hayashi
Journal:  J Biochem       Date:  1995-09       Impact factor: 3.387

3.  Catalytic reactions involving azomethines. XII. Transamination of 1-methyl-3-hydroxy-4-formylpyridinium chloride.

Authors:  J R Maley; T C Bruice
Journal:  Arch Biochem Biophys       Date:  1970-01       Impact factor: 4.013

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

Authors:  J P Shaw; G A Petsko; D Ringe
Journal:  Biochemistry       Date:  1997-02-11       Impact factor: 3.162

5.  Kinetics and equilibria for the reactions of coenzymes with wild type and the Y70F mutant of Escherichia coli aspartate aminotransferase.

Authors:  M D Toney; J F Kirsch
Journal:  Biochemistry       Date:  1991-07-30       Impact factor: 3.162

Review 6.  Reaction specificity in pyridoxal phosphate enzymes.

Authors:  Michael D Toney
Journal:  Arch Biochem Biophys       Date:  2005-01-01       Impact factor: 4.013

7.  Aspartate-279 in aminolevulinate synthase affects enzyme catalysis through enhancing the function of the pyridoxal 5'-phosphate cofactor.

Authors:  J Gong; G A Hunter; G C Ferreira
Journal:  Biochemistry       Date:  1998-03-10       Impact factor: 3.162

8.  Characterization of the apparent negative co-operativity induced in Escherichia coli aspartate aminotransferase by the replacement of Asp222 with alanine. Evidence for an extremely slow conformational change.

Authors:  J J Onuffer; J F Kirsch
Journal:  Protein Eng       Date:  1994-03

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

Authors:  J E Dixon; T C Bruice
Journal:  Biochemistry       Date:  1973-11-06       Impact factor: 3.162

10.  Role of an active site residue analyzed by combination of mutagenesis and coenzyme analog.

Authors:  T Yano; Y Hinoue; V J Chen; D E Metzler; I Miyahara; K Hirotsu; H Kagamiyama
Journal:  J Mol Biol       Date:  1993-12-20       Impact factor: 5.469

View more
  5 in total

Review 1.  Aspartate aminotransferase: an old dog teaches new tricks.

Authors:  Michael D Toney
Journal:  Arch Biochem Biophys       Date:  2013-10-09       Impact factor: 4.013

Review 2.  Controlling reaction specificity in pyridoxal phosphate enzymes.

Authors:  Michael D Toney
Journal:  Biochim Biophys Acta       Date:  2011-06-06

3.  Ground-state electronic destabilization via hyperconjugation in aspartate aminotransferase.

Authors:  Wait R Griswold; Joan Nieto Castro; Andrew J Fisher; Michael D Toney
Journal:  J Am Chem Soc       Date:  2012-05-10       Impact factor: 15.419

4.  The Nitrogen Atom of Vitamin B6 Is Essential for the Catalysis of Radical Aminomutases.

Authors:  Amarendra Nath Maity; Jun-Ru Chen; Quan-Yuan Li; Shyue-Chu Ke
Journal:  Int J Mol Sci       Date:  2022-05-06       Impact factor: 6.208

Review 5.  Large-scale domain motions and pyridoxal-5'-phosphate assisted radical catalysis in coenzyme B12-dependent aminomutases.

Authors:  Amarendra Nath Maity; Yung-Han Chen; Shyue-Chu Ke
Journal:  Int J Mol Sci       Date:  2014-02-20       Impact factor: 5.923

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.