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

SUBMITTER: Lowe J 

PROVIDER: S-EPMC7341106 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature