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Two‐Step One‐Pot Synthesis of Pinoresinol from Eugenol in an Enzymatic Cascade
Author(s) -
Ricklefs Esther,
Girhard Marco,
Koschorreck Katja,
Smit Martha S.,
Urlacher Vlada B.
Publication year - 2015
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201500182
Subject(s) - pinoresinol , coniferyl alcohol , lignan , chemistry , eugenol , bioconversion , laccase , isoeugenol , enzyme , organic chemistry , stereochemistry , fermentation
The phytoestrogen pinoresinol is a high‐value compound that has a protective effect against diverse health disorders, and thus is of interest for the pharmaceutical industry. Isolation of pinoresinol from plants suffers from low yields, and its chemical synthesis involves several work‐up steps. In this study we devised a novel two‐step one‐pot enzymatic cascade combining a vanillyl‐alcohol oxidase and a laccase for the production of pinoresinol from eugenol via the intermediate coniferyl alcohol. Along with the well‐characterized vanillyl‐alcohol oxidase from Penicillium simplicissimum used to catalyze the oxidation of eugenol, enzyme screening revealed three bacterial laccases that were appropriate for the synthesis of pinoresinol from coniferyl alcohol. The cascade was optimized regarding enzyme ratios, pH value, and the presence of organic solvents. Under optimized conditions, pinoresinol concentration achieved 4.4 m M (1.6 g l −1 ), and this compound was isolated and analyzed.