Back to Search
Start Over
Regio‐ and Enantio‐selective Chemo‐enzymatic C−H‐Lactonization of Decanoic Acid to (S)‐δ‐Decalactone.
- Source :
-
Angewandte Chemie . 4/16/2019, Vol. 131 Issue 17, p5724-5727. 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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *LACTONES
*DECANOIC acid
*HYDROXYLATION
*CYTOCHROME P-450
*MONOOXYGENASES
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 131
- Issue :
- 17
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 135796004
- Full Text :
- https://doi.org/10.1002/ange.201901242