Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 2, Pages 229-241Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101073
Keywords
Amino acids; Amines; Transamination; Rearrangement; Chiral resolution
Categories
Funding
- Natural Sciences and Engineering Research Council of Canada
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Biomimetic studies of pyridoxal and pyridoxamine models are of both fundamental and practical interest. This review examines (i) deracemization of alpha-amino acids with a chiral pyridoxal model, (ii) sensing of chirality of small molecules including alpha-, beta-, and gamma-amino acids, peptides, amino alcohols and diamines with an achiral pyridoxal model and (iii) stereospecific synthesis of chiral diamines with a chiral pyridoxamine model. A binol-based aldehyde is useful as a chiral pyridoxal model to deracemize a variety of alpha-amino acids to make D-amino acids. 2,2'-Dihydroxybenzophenone is useful as an achiral pyridoxal model for sensing the chirality of the above-mentioned small molecules in a unified way. Bis(2-hydroxyphenyl)-ethylenediamine (hpen) is useful as a chiral pyridoxamine model for making chiral diamines. Weak forces (H-bonding, steric and electronic effects) involved in transamination reactions with pyridoxamine for the synthesis of amino acids are compared with those for the diaza-Cope rearrangement reaction with hpen for the synthesis of chiral diamines. Both experimental and computational methods are used to analyze the biomimetic systems.
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