35875-13-9Relevant articles and documents
Regio- and Enantio-selective Chemo-enzymatic C?H-Lactonization of Decanoic Acid to (S)-δ-Decalactone
Manning, Jack,Tavanti, Michele,Porter, Joanne L.,Kress, Nico,De Visser, Sam P.,Turner, Nicholas J.,Flitsch, Sabine L.
, p. 5668 - 5671 (2019/03/29)
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.
Microbial Transformation of 12-Hydroxyoctadecanoic Acid to 5-n-Hexyl-Tetrahydrofuran-2-Acetic Acid
Huang, J.-K.,Keudell, K. C.,Zhao, J.,Klopfenstein, W. E.,Wen, L.,et al.
, p. 323 - 326 (2007/10/02)
Stationary-phase cells of a corynebacterium (FUI-2) and a bacillus (NRRL B-14864) isolate, when grown aerobically in 1percent YE medium at 25 deg C, converted 12-hydroxystearic acid to a major compound, 5-n-hexyl-tetrahydrofuran-2-acetic acid, and other intermediate and minor compounds (6-hydroxydodecanoic acid, 4-hydroxydecanoic acid, 4-ketodecanoic acid and γ-decanolactone).The yields of 5-n-hexyl-tetrahydrofuran-2-acetic acid, 4-hydroxydecanoic acid, and γ-decanolactone, by Bacillus lentus NRRL B-14864 were 43percent, 18percent and 5percent, respectively, after 2.5 d of incubation. Key Words: Bacillus lentus, corynebacterium, D-(+)-12-hydroxy-octadecanoic acid, D-(+)-12-hydroxystearic acid, γ-decanolactone, 4-hydroxydecanoic acid, 6-hydroxydodecanoic acid, 4-ketodecanoic acid, 5-n-hexyl-tetrahydrofuran-2-acetic acid.