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Premium 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 year2019
Publication title
angewandte chemie
Resource typeJournals
PublisherWiley
Abstract 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.
Subject(s)catalysis , chemistry , cytochrome p450 , decanoic acid , double bond , enzyme , hydroxylation , monooxygenase , organic chemistry , regioselectivity , stereochemistry , stereoselectivity
Language(s)English
eISSN1521-3757
pISSN0044-8249
DOI10.1002/ange.201901242

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