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Tailoring D-amino Acid Oxidase From the Pig Kidney to R-stereoselective Amine Oxidase and Its Use in the Deracemization of α-methylbenzylamine

Tailoring D-amino Acid Oxidase From the Pig Kidney to R-stereoselective Amine Oxidase and Its Use in the Deracemization of α-methylbenzylamine

Kazuyuki Yasukawa, Shogo Nakano, Yasuhisa Asano

Angew Chem Int Ed Engl. 2014 Apr 22;53(17):4428-31.

PMID: 24644036

Abstract:

The deracemization of racemic amines to yield enantioenriched amines using S-stereoselective amine oxidases (AOx) has recently been attracting attention. However, R-stereoselective AOx that are suitable for deracemization have not yet been identified. An R-stereoselective AOx was now evolved from porcine kidney D-amino acid oxidase (pkDAO) and subsequently use for the deracemization of racemic amines. The engineered pkDAO, which was obtained by directed evolution, displayed a markedly changed substrate specificity towards R amines. The mutant enzyme exhibited a high preference towards the substrate α-methylbenzylamine and was used to synthesize the S amine through deracemization. The findings of this study indicate that further investigations on the structure-activity relationship of AOx are warranted and also provide a new method for biotransformations in organic synthesis.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2627863	(S)-(−)-α-Methylbenzylamine		2627-86-3	Price

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