Biocatalyst for the functionalization of resin acids
Resin acid derivatives are promising bioactive agents as they exhibit interesting biological and pharmaceutical properties such as antimicrobial, antiviral, antifungal, anti-cancer as well as anti-mutagenic activity. The regio- and stereoselective functionalization of terpenes is hard to achieve by means of classical organic syntheses since reliable methods for the conversion of unactivated carbon atoms are missing. The ability of cytochrome P450s to oxidize such unactivated C-H bonds makes them versatile enzymes for biotechnological applications. Compared to classical chemical approaches, they allow the synthesis or modification, respectively, of complex natural substances in a time-efficient manner, going along with environmental and economic benefits.
Scientists of Saarland University have found a cytochrome P450 that catalyzes the selective conversion of abietic acid into 15-hydroxyabietic acid. The functionalization of C15 is hardly accessible by means of classical organic synthesis as it is unactivated. Besides abietic acid, other diterpene resin acids of the abietane- and pimarane-type like dehydroabietic acid and isopimaric acid were found to be suitable substrates for such conversions induced by the beforehand mentioned enzyme.
This newly developed synthetic approach opens up the possibility to easily synthesize hydroxylated and epoxidized forms of diterpene resin acids. Considering the biological and pharmaceutical activities of these compounds, a compound library with a broad range of possible applications could be established. Hence, further research becomes easier. For example, 15-hydroxyabietic acid is the immediate precursor within the chemical synthesis of 15-hydroxyperoxyabietic acid, the main allergen of the resin kolophonium and one of the most common contact allergens. Therefore, the invention serves as a basis for the development of test systems such as allergy tests.
- Functionalization of unactivated carbon atoms within complex natural substances that can hardly be achieved by classical organic syntheses.
- High stereo- and regioselectivity of the reactions Broad band of suitable substrates.
- Time and cost efficient No toxic side products as in classical organic chemistry.