From a Biosynthetic Pathway toward a Biocatalytic Process and Chemocatalytic Modifications: Three-Step Enzymatic Cascade to the Plant Metabolite cis -(+)-12-OPDA and Metathesis-Derived Products
Abstract
A biotechnological approach toward the plant metabolite and regulator cis-(+)-12-oxophytodienoic acid (cis-(+)-12-OPDA) in a one-pot process with >99% conversion, at least 90% selectivity and ≤10% of side products as well as a high diastereoselectivity (leading to d.r. of at least 90:10) is reported. The optimized organic-synthetic enzyme cascade for preparing this bioactive and commercial molecule with pharmaceutical relevance on a gram per L scale is designed based on its biosynthetic pathway starting from cheap and readily accessible linolenic acid. Toward this end, a recombinant biocatalyst system has been prepared for carrying out the most critical two key steps in a tailored manner, thus avoiding sensitive intermediate decomposition. Furthermore, cis-(+)-12-OPDA is successfully modified via a cross-alkene metathesis reaction with conversions of up to >99%, leading to a compound library of new cis-(+)-12-OPDA derivatives with different substitution pattern of the side chain at the 2-position. By means of such a combined biotechnological and chemocatalytic route, a straightforward approach to a structurally unique oxylipin library is realized, which would be highly difficult or not accessible by pure chemical and biotechnol...Continue Reading
References
Citations
Methods Mentioned
Related Concepts
Related Feeds
Bioinformatics in Biomedicine
Bioinformatics in biomedicine incorporates computer science, biology, chemistry, medicine, mathematics and statistics. Discover the latest research on bioinformatics in biomedicine here.