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Stereoselective Enzyme Cascades: An Efficient Synthesis of Chiral γ-Butyrolactones

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논문

Stereoselective Enzyme Cascades: An Efficient Synthesis of Chiral γ-Butyrolactones

학술지

ACS catalysis

저자명

Classen, Thomas; Korpak, Margarete; Schö lzel, Melanie; Pietruszka, Jö rg

초록

<P>A one-pot consecutive two-enzyme sequential cascade toward chiral &gamma;-butyrolactones using an enoate reductase as well as alcohol dehydrogenases in combination with a glucose dehydrogenase is reported. In this scalable process, the products were obtained in high yield (up to 90%) and with perfect enantioselectivity (98&rarr;99% ee). The starting materials, ethyl 4-oxo-pent-2-enoates, are readily accessible via Wittig-type reactions. Furthermore, the stereoselectivity of the enoate reductase catalyzed reaction has been studied in detail, leading to deeper insights into the mechanism of this enzyme.</P><P><B>Graphic Abstract</B><BR><IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/accacs/2014/accacs.2014.4.issue-5/cs5000262/production/images/medium/cs-2014-000262_0010.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/cs5000262'>ACS Electronic Supporting Info</A></P>

발행연도

2014

발행기관

American Chemical Society

ISSN

2155-5435

4

5

페이지

pp.1321-1331

주제어

enzymes; enantioselective catalysis; reaction cascades; reductases; lactones

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논문; 2014-03-31

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