BioChem - DOS

Regio- and Enantio-selective Chemo-enzymatic C-H-Lactonization of Decanoic Acid to (S)-δ-Decalactone

Angewandte Chemie. international edition

Manning, Jack; Tavanti, Michele; Porter, Joanne L.; Kress, Nico; De Visser, Sam P.; Turner, Nicholas J.; Flitsch, Sabine L.

<P><B>Abstract</B></P><P>The conversion of saturated fatty acids to high value chiral hydroxy&#8208;acids and lactones poses a number of synthetic challenges: the activation of unreactive C&minus;H bonds and the need for regio&#8208; and stereoselectivity. Here the first example of a wild&#8208;type cytochrome P450 monooxygenase (CYP116B46 from Tepidiphilus thermophilus) capable of enantio&#8208; and regioselective C5 hydroxylation of decanoic acid <B>1</B> to (<I>S</I>)&#8208;5&#8208;hydroxydecanoic acid <B>2</B> is reported. Subsequent lactonization yields (<I>S</I>)&#8208;&delta;&#8208;decalactone <B>3</B>, a high value fragrance compound, with greater than 90 % <I>ee</I>. Docking studies provide a rationale for the high regio&#8208; and enantioselectivity of the reaction.</P>

2019

1433-7851

1521-3773

58

17

pp.5668-5671

10.1002/anie.201901242

http://click.ndsl.kr/servlet/OpenAPIDetailView?keyValue=05787966&target=NART&cn=NART96279124

biocatalysis; cytochrome P450; fatty acids; lactones; regioselectivity