California Institute of Technology

Provivi, Inc.

Mike M Y Chen

Peter Meinhold

Frances H Arnold

Matthew W Peters

Rudi Fasan

Pedro Coelho

Vu Bui

Thomas Heel

Catherine Mee-Hie Cho

This invention relates to modified hydroxylases. The invention further relates to cells expressing such modified hydroxylases and methods of producing hydroxylated alkanes by contacting a suitable substrate with such cells.

Alkane oxidation by modified hydroxylases

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.

Synthesis of olefinic alcohols via enzymatic terminal hydroxylation

The present invention provides methods for synthesizing pyrethroid compounds. The methods include forming a first reaction comprising an olefin and an allethrolone-type unsaturated alcohol under conditions sufficient to form a metathesis product and converting the metathesis product to the pyrethroid. Methods of the invention can be used to prepare compounds including pyrethrin I, cinerin I, jasmolin I, pyrethrin II, cinerin II, and jasmolin II as well as other synthetic pyrethroid compounds. Insecticidal compositions and methods for controlling insects are also described.

Synthesis of pyrethroids and pyrethroid-containing compositions

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Pasadena, CA, United States of America

Mike M Y Chen