1337992-51-4Relevant academic research and scientific papers
Synthesis of enantiomerically enriched dimers of vinylphenols by tandem action of laccases and lipases
Gavezzotti, Paolo,Navarra, Cristina,Caufin, Stefania,Danieli, Bruno,Magrone, Pietro,Monti, Daniela,Riva, Sergio
, p. 2421 - 2430 (2011)
The tandem use of laccases and lipases has been exploited for the simple preparative synthesis of enantiomerically enriched dimeric phenols. Laccase-catalyzed oxidation of isoeugenol (1) and vinylguaiacol (7) in biphasic systems gave as main products the racemic compounds 6 and 8, possessing structures similar to the β-5 dimers found in lignin. The synthesis of enantiomerically enriched 6 and 8 could be achieved by alcoholysis reactions catalyzed by commercial preparations of lipases in organic solvents. Although the E values were quite low (due to the "remote" stereocenters to be discriminated), the enantio-complementary behavior of the tested lipases allowed the simple isolation of the target compounds with ee up to 90%. It is noteworthy that these results have been achieved in vitro exploiting commercially available enzymes, without using the so-called "dirigent" proteins evolved by nature to direct the enantioselective coupling of phenols in vivo. Copyright
