Synthesis of Enantiomerically Enriched Dimers of Vinylphenols by Tandem Action of Laccases and Lipases

Autor: Sergio Riva, Daniela Monti, Bruno Danieli, Stefania Caufin, Paolo Gavezzotti, Pietro Magrone, Cristina Navarra
Rok vydání: 2011
Předmět:
Zdroj: Advanced synthesis & catalysis
353 (2011): 2421–2430. doi:10.1002/adsc.201100413
info:cnr-pdr/source/autori:Gavezzotti, Paolo; Navarra, Cristina; Caufin, Stefania; Danieli, Bruno; Magrone, Pietro; Monti, Daniela; Riva, Sergio/titolo:Synthesis of Enantiomerically Enriched Dimers of Vinylphenols by Tandem Action of Laccases and Lipases/doi:10.1002%2Fadsc.201100413/rivista:Advanced synthesis & catalysis (Print)/anno:2011/pagina_da:2421/pagina_a:2430/intervallo_pagine:2421–2430/volume:353
ISSN: 1615-4150
DOI: 10.1002/adsc.201100413
Popis: 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 beta-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.
Databáze: OpenAIRE
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