Synthesis of olefinic alcohols via enzymatic terminal hydroxylation
US10202620B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Sep 3, 2015 |
| Grant date | Feb 12, 2019 |
| Priority date | — |
| Expiry date | Sep 3, 2035 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2531/24
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.