BioChem - DOS

Enantiomerically Pure 3-Aryl- and 3-Hetaryl-2-hydroxypropanoic Acids by Chemoenzymatic Reduction of 2-Oxo Acids

Journal of organic chemistry

Sivanathan, Sivatharushan; Kö rber, Florian; Tent, Jannis Aron; Werner, Svenja; Scherkenbeck, Jü rgen

<P>Phenyllactic acids are found in numerous natural products as well as in active substances used in medicine or plant protection. Enantiomerically pure phenyllactic acids are available by transition-metal-catalyzed hydrogenations or chemoenzymatic reductions of the corresponding 3-aryl-2-oxopropanoic acids. We show here that <SMALL>d</SMALL>-lactate dehydrogenase from <I>Staphylococcus epidermidis</I> reduces a broad spectrum of 2-oxo acids, which are difficult substrates for transition-metal-catalyzed reactions, with excellent enantioselectivities in a simple experimental setup.</P><P><B>Graphic Abstract</B><BR><IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/joceah/2015/joceah.2015.80.issue-5/jo502529g/production/images/medium/jo-2014-02529g_0009.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/jo502529g'>ACS Electronic Supporting Info</A></P>

2015

American Chemical Society

0022-3263

1520-6904

80

5

pp.2554-2561

10.1021/jo502529g

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