7370-36-7Relevant academic research and scientific papers
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.
Improved synthesis of γ-lactones from cyclopropyl cyanoesters
Patel, Nandini C.,Schwarz, Jacob B.,Islam, Khondaker,Miller, Whitney,Tran, Tuan P.,Wei, Yunjing
, p. 2209 - 2215 (2011/07/07)
Cyclopropyl cyanoesters 2 were reliably converted to c-lactones 4 on treatment with aqueous sulfuric acid. The cyanoesters could be easily prepared from ketones or aldehydes in two steps, making this process particularly attractive from an efficiency standpoint. Copyright
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.
