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Dynamic Kinetic Resolution of α-Aminonitriles to Form Chiral α-Amino Acids

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논문

Dynamic Kinetic Resolution of α-Aminonitriles to Form Chiral α-Amino Acids

학술지

Advanced synthesis & catalysis

저자명

Yasukawa, Kazuyuki; Hasemi, Ryuji; Asano, Yasuhisa

초록

<P><B>Abstract</B></P><P>We have succeeded in the enzymatic synthesis of (<I>R</I>)&#8208;&alpha;&#8208;aminobutyric acid from racemic &alpha;&#8208;aminobutyronitrile. This has been demonstrated by the use of non&#8208;stereoselective nitrile hydratase (NHase) from <I>Rhodococcus opacus</I> 71D, <SMALL>D</SMALL>&#8208;aminopeptidase from <I>Ochrobactrum anthropi</I> C1&#8208;38 and &alpha;&#8208;amino&#8208;&epsilon;&#8208;caprolactam (ACL) racemase from <I>Achromobacter obae</I>. Racemic &alpha;&#8208;aminobutyronitrile was completely converted in 6 h at 30&thinsp;&deg;C to (<I>R</I>)&#8208;&alpha;&#8208;aminobutyric acid whose optical purity was more than 99%. (<I>S</I>)&#8208;&alpha;&#8208;Aminobutyric acid was also synthesized from &alpha;&#8208;aminobutyronitrile by NHase, ACL racemase and <SMALL>L</SMALL>&#8208;amino acid amidase from <I>Brevundimonas diminuta</I> TPU 5720. In a similar manner, other (<I>R</I>)&#8208; or (<I>S</I>)&#8208;&alpha;&#8208;amino acids with more than 97.5% <I>ee</I> could be synthesized from the corresponding &alpha;&#8208;aminonitriles. This is the first report on the dynamic kinetic resolution (DKR) of &alpha;&#8208;aminonitriles to form chiral &alpha;&#8208;amino acids. The key enzyme in this DKR is non&#8208;stereoselective NHase, which had been newly screened from soil samples, and its gene cloned.</P>

발행연도

2011

ISSN

1615-4150

ISSN

1615-4169

353

13

페이지

pp.2328-2332

주제어

amino acids; biotransformation; dynamic kinetic resolution; nitrile hydratase

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1 2023-12-11
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논문; 2011-08-26

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