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Regio‐ and Enantio‐selective Chemo‐enzymatic C−H‐Lactonization of Decanoic Acid to (S)‐δ‐Decalactone.
- Source :
- Angewandte Chemie International Edition; 4/16/2019, Vol. 58 Issue 17, p5668-5671, 4p
- Publication Year :
- 2019
-
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. The cytochrome P450 monooxygenase, CYP116B46, from Tepidiphilus thermophilus is capable of enantio‐ and regioselective C5 hydroxylation of decanoic acid 1 to (S)‐5‐hydroxydecanoic acid 2. 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. [ABSTRACT FROM AUTHOR]
- Subjects :
- DECANOIC acid
RACEMIC mixtures
SATURATED fatty acids
CYTOCHROME P-450
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 58
- Issue :
- 17
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 135794240
- Full Text :
- https://doi.org/10.1002/anie.201901242