Literature DB >> 16930073

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

Krisztina Toth1, Lauren M Gaskell, John P Richard.   

Abstract

The 5'-deoxypyridoxal stabilized glycine carbanion has been generated in water at neutral and mildly basic pH. At pH < 7, this carbanion reacts mainly with the carbonyl carbon of 1 to form a stable Claisen-type adduct. At pH > or = 8, this carbanion reacts with the iminium carbon of the pyridoxal-glycine iminium ion to form the second Claisen-type adduct 3 as the major reaction product.

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Year:  2006        PMID： 16930073     DOI： 10.1021/jo061090e

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  5 in total

Review 1.  The PLP cofactor: lessons from studies on model reactions.

Authors:  John P Richard; Tina L Amyes; Juan Crugeiras; Ana Rios
Journal:  Biochim Biophys Acta       Date:  2010-12-20

2.  Alanine-dependent reactions of 5'-deoxypyridoxal in water.

Authors:  Maybelle K Go; John P Richard
Journal:  Bioorg Chem       Date:  2008-09-21       Impact factor: 5.275

3.  Covalent catalysis by pyridoxal: evaluation of the effect of the cofactor on the carbon acidity of glycine.

Authors:  Krisztina Toth; John P Richard
Journal:  J Am Chem Soc       Date:  2007-02-14       Impact factor: 15.419

Review 4.  Pyridoxal 5'-phosphate: electrophilic catalyst extraordinaire.

Authors:  John P Richard; Tina L Amyes; Juan Crugeiras; Ana Rios
Journal:  Curr Opin Chem Biol       Date:  2009-07-27       Impact factor: 8.822

5.  Substituent Effects on Carbon Acidity in Aqueous Solution and at Enzyme Active Sites.

Authors:  Tina L Amyes; John P Richard
Journal:  Synlett       Date:  2017-03-10       Impact factor: 2.454
  5 in total

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