7370-36-7Relevant articles and documents
CYP505E3: A Novel Self-Sufficient ω-7 In-Chain Hydroxylase
Maseme, Mpeyake Jacob,Opperman, Diederik Johannes,Pennec, Alizé,Smit, Martha Sophia,van Marwijk, Jacqueline
supporting information, p. 10359 - 10362 (2020/04/23)
The self-sufficient cytochrome P450 monooxygenase CYP505E3 from Aspergillus terreus catalyzes the regioselective in-chain hydroxylation of alkanes, fatty alcohols, and fatty acids at the ω-7 position. It is the first reported P450 to give regioselective in-chain ω-7 hydroxylation of C10–C16 n-alkanes, thereby enabling the one step biocatalytic synthesis of rare alcohols such as 5-dodecanol and 7-tetradecanol. It shows more than 70 percent regioselectivity for the eighth carbon from one methyl terminus, and displays remarkably high activity towards decane (TTN≈8000) and dodecane (TTN≈2000). CYP505E3 can be used to synthesize the high-value flavour compound δ-dodecalactone via two routes: 1) conversion of dodecanoic acid into 5-hydroxydodecanoic acid (24 percent regioselectivity), which at low pH lactonises to δ-dodecalactone, and 2) conversion of 1-dodecanol into 1,5-dodecanediol (55 percent regioselectivity), which can be converted into δ-dodecalactone by horse liver alcohol dehydrogenase.
SYNTHETIC INVESTIGATIONS IN THE REGION OF INSECT ATTRACTANTS (SEX ATTRACTANTS). IX. SYNTHESIS OF cis-7-NONADECEN-11-ONE AND cis-7-EICOSEN-11-ONE - COMPONENTS OF THE SEX PHEROMONE OF THE PEACH FRUIT MOTH Carposina niponensis W.
Sorochinskaya, A. M.,Kovalev, B. G.,Avdeeva, L. A.
, p. 277 - 283 (2007/10/02)
The synthesis of cis-7-nonadecen-11-one and cis-7-eicosen-11-one, components of the sex pheromone of the peach fruit moth Carposina niponensis W., from furfural is described.
