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Biological Implications of Oxidation and Unidirectional Chiral Inversion of D-amino Acids

[ Vol. 13 , Issue. 3 ]


Yong-Xiang Wang, Nian Gong, Yan-Fei Xin, Bin Hao, Xiang-Jun Zhou and Catherine C.Y. Pang   Pages 321 - 331 ( 11 )


Recent progress in chiral separation of D- and L-amino acids by chromatography ascertained the presence of several free Damino acids in a variety of mammals including humans. Unidirectional chiral inversion of many D-amino acid analogs such as exogenous NG-nitro-D-arginine (D-NNA), endogenous D-leucine, D-phenylanine and D-methionine have been shown to take place with inversion rates of 4-90%, probably dependent on various species D-amino acid oxidase (DAAO) enzymatic activities. DAAO is known to catalyze the oxidative deamination of neutral and basic D-amino acids to their corresponding α-keto acids, hydrogen peroxide and ammonia, and is responsible for the chiral inversion. This review provides an overview of recent research in this area: 1) oxidation and chiral inversion of several D-amino acid analogs in the body; 2) the indispensable but insufficient role of DAAO particularly in the kidneys and brain for the oxidation and chiral inversion of D-amino acids analogs; and 3) unidentified transaminase(s) responsible for the second step of chiral inversion. The review also discusses the physiological significance of oxidation and chiral inversion of D-amino acids, which is still a subject of dispute.


D-amino acid, D-amino acid oxidase (DAAO), kidney, NG-nitro-D-arginine (D-NNA), transaminase, unidirectional chiral inversion, proteinogenic amino acids, chromatography, L-configuration, racemization


King's Lab, School of Pharmacy, Shanghai Jiao Tong University, NO. 6 Biomedicine Building (Suite 106), 800 Dongchuan Road, Shanghai 200240, China

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