CYP505E3 – a novel self-sufficient ω-7 in-chain hydroxylase.
Angew Chem Int Ed Engl. 2020 Mar 08;:
Authors: Smit MS, Maseme MJ, Pennec A, van Marwijk J, Opperman DJ
A self-sufficient cytochrome P450 monooxygenase, CYP505E3, identified in Aspergillus terreus catalyzes regioselective in-chain hydroxylation of alkanes, fatty alcohols and fatty acids at the ω-7 position. It thus hydroxylates C10 to C16 alkanes with > 70 % regioselectivity at the eighth carbon from one methyl terminus, also displaying remarkably high activity towards decane (TTN ≈ 8 000) and dodecane (TTN ≈ 2 000). CYP505E3 converts dodecanoic acid to 5-hydroxydodecanoic acid (24 % regioselectivity), which at low pH lactonises to δ-dodecalactone. With 1-dodecanol as substrate it displays 55% regioselectivity towards the ω-7 position to yield 1,5-dodecanediol, which was converted to δ-dodecalactone by horse liver alcohol dehydrogenase (HLADH).
PMID: 32147902 [PubMed – as supplied by publisher]