CYP505E3: A Novel Self-Sufficient omega-7 In-Chain Hydroxylase

摘要

The self-sufficient cytochrome P450 monooxygenase CYP505E3 fromAspergillus terreuscatalyzes the regioselective in-chain hydroxylation of alkanes, fatty alcohols, and fatty acids at the omega-7 position. It is the first reported P450 to give regioselective in-chain omega-7 hydroxylation of C10-C16n-alkanes, thereby enabling the one step biocatalytic synthesis of rare alcohols such as 5-dodecanol and 7-tetradecanol. It shows more than 70 % regioselectivity for the eighth carbon from one methyl terminus, and displays remarkably high activity towards decane (TTN approximate to 8000) and dodecane (TTN approximate to 2000). CYP505E3 can be used to synthesize the high-value flavour compound delta-dodecalactone via two routes: 1) conversion of dodecanoic acid into 5-hydroxydodecanoic acid (24 % regioselectivity), which at low pH lactonises to delta-dodecalactone, and 2) conversion of 1-dodecanol into 1,5-dodecanediol (55 % regioselectivity), which can be converted into delta-dodecalactone by horse liver alcohol dehydrogenase.