In:
Angewandte Chemie, Wiley, Vol. 131, No. 17 ( 2019-04-16), p. 5724-5727
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.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v131.17
DOI:
10.1002/ange.201901242
Language:
English
Publisher:
Wiley
Publication Date:
2019
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505868-5
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514305-6
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505872-7
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1479266-7
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506259-7
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