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Biocatalytic Asymmetric Synthesis of Optically Pure Aromatic Propargylic Amines Employing ω-Transaminases

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논문

Biocatalytic Asymmetric Synthesis of Optically Pure Aromatic Propargylic Amines Employing ω-Transaminases

학술지

Advanced synthesis & catalysis

저자명

Schmidt, Nina G.; Simon, Robert C.; Kroutil, Wolfgang

초록

<P><B>Abstract</B></P><P>The asymmetric reductive bio&#8208;amination of prochiral aromatic propargyl ketones led to the corresponding amines in optically pure form (<I>ee</I>>99%). The (<I>R</I>)&#8208; as well as the (<I>S</I>)&#8208;enantiomers of the propargylic amines were obtained, employing either (<I>R</I>)&#8208;selective &omega;&#8208;transaminases (&omega;&#8208;TAs) originating from <I>Arthrobacter</I> sp. and <I>Aspergillus terreus</I> or an (<I>S</I>)&#8208;selective &omega;&#8208;TA from <I>Chromobacterium violaceum</I>. The product propargylic amines were obtained with high conversions (up to 99%). To simplify product isolation, protection of the free amino group to the corresponding acetamides or benzamides was performed without loss of optical puritiy. The final products were isolated in moderate to good yields (33&ndash;67% over two steps) in optical pure form without additional purification steps. Although propargyl ketones are described in the literature to be irreversible inhibitors for aminotransferases, suitable &omega;&#8208;transaminases were identified for the amination of these compounds.</P>

발행연도

2015

ISSN

1615-4150

ISSN

1615-4169

357

8

페이지

pp.1815-1821

주제어

amines; asymmetric catalysis; biotransformations; enzymes; propargylic amines

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1 2023-12-11
3 2023-12-11

논문; 2015-04-29

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