Monooxygenase systems for the regio- and stereo- selective modification of terpenes
Terpene and terpenoids are the most diverse family of natural products serving a range of important functions. Regio- or stereoselective functionalization of terpenes are one of the main goals of synthetic organic chemistry, which are possible through radical reactions but are not selective enough to introduce the desired chiral alcohol function into those compounds. Cytochrome P450 monooxygenases are versatile biocatalysts and are capable of performing selective oxidations of organic molecules.
Inventors of Saarland University were able to generate a patent portfolio dealing with different biocatalysts which are able to catalyze terpenes in a stereo-selective way.
The Cytochrome P450 CYP109D1 from Sorangium cellulosum So ce56 was found to function as a biocatalyst for the highly regioselective hydroxylation and/or epoxidation of mono-or sesquiterpenes. The Cytochrome P450 CYP106A2 from Bacillus megaterium was found to function as a regioselective hydroxylase for diterpene, i.e. abietic acid. This enzyme was also identified to hydroxylate the anti-inflammatory pentacyclic triterpene 11-Keto-ß-boswellic acid (KBE)
Mono-or sesquiterpene are substantial aroma components of floral scents and thus attract the attention of flavour and fragrance industry. Besides this, the sesquiterpene ionones are also appreciated as synthetic building blocks for the synthesis of carotenoids and vitamin A (retinol). Diterpene and pentacyclic triterpene occur widely in trees and plants. They are the main components of rosin. The abietane diterpene are used in lacquers, varnishes, and soaps, while the pentacyclic triterpene show anti- inflammatory activities.
- enzymes cloned
- successfully expressed
- upscale possible
- alternative to classical organic chemistry with toxic side products
- application of renewable resourceswhole-cell systems allow for the stabilization of the P450 system and the simultaneous regeneration of the cofactor saving costs and time
- high regio- and stereospecificity of the reaction for the production of fine chemicals or pharmaceuticals