Mimicking Nature to Make Unnatural Amino Acids and Chiral Diamines

Autor:	Hyunwoo Kim, Leo Mui, Jik Chin, Soon Mog So
Rok vydání:	2011
Předmět:	chemistry.chemical_classification Stereochemistry Transamination Organic Chemistry Aldehyde Amino acid chemistry.chemical_compound Stereospecificity chemistry Rearrangement reaction Pyridoxamine Physical and Theoretical Chemistry Chirality (chemistry) Pyridoxal
Zdroj:	European Journal of Organic Chemistry. 2012:229-241
ISSN:	1099-0690 1434-193X
Popis:	Biomimetic studies of pyridoxal and pyridoxamine models are of both fundamental and practical interest. This review examines (i) deracemization of α-amino acids with a chiral pyridoxal model, (ii) sensing of chirality of small molecules including α-, β-, and γ-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 α-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.
Databáze:	OpenAIRE
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