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Regio‐ and Enantio‐selective Chemo‐enzymatic C−H‐Lactonization of Decanoic Acid to ( S )‐δ‐Decalactone
Author(s) -
Manning Jack,
Tavanti Michele,
Porter Joanne L.,
Kress Nico,
De Visser Sam P.,
Turner Nicholas J.,
Flitsch Sabine L.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201901242
Subject(s) - decanoic acid , chemistry , hydroxylation , regioselectivity , monooxygenase , stereoselectivity , stereochemistry , cytochrome p450 , enzyme , organic chemistry , catalysis
The conversion of saturated fatty acids to high value chiral hydroxy‐acids and lactones poses a number of synthetic challenges: the activation of unreactive C−H bonds and the need for regio‐ and stereoselectivity. Here the first example of a wild‐type cytochrome P450 monooxygenase (CYP116B46 from Tepidiphilus thermophilus) capable of enantio‐ and regioselective C5 hydroxylation of decanoic acid 1 to ( S )‐5‐hydroxydecanoic acid 2 is reported. Subsequent lactonization yields ( S )‐δ‐decalactone 3 , a high value fragrance compound, with greater than 90 % ee . Docking studies provide a rationale for the high regio‐ and enantioselectivity of the reaction.
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