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Controlling the polymerization of coniferyl alcohol with cyclodextrins

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Abstract

The mono-electronic oxidation of coniferyl alcohol leads to the formation of phenoxy radicals and ultimately to the synthesis of dimeric lignan and neo-lignan products. Coniferyl alcohol and dimeric products are all potential guests for cyclodextrins (CDs) to form noncovalent host–guest inclusion complexes. Herein, the influence of CDs with different cavity volumes (i.e., α, β or CD) on the laccase-driven oxidation of coniferyl alcohol is studied. We clearly show that βCD interacts with the dimeric products and selectively prevents their further oxidation by the enzyme. Moreover, amongst the three dimeric products generated, the system containing a laccase and βCD allows the selective enrichment of pinoresinol; this behaviour is similar to that of plant dirigent proteins.

Graphical abstract: Controlling the polymerization of coniferyl alcohol with cyclodextrins

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Publication details

The article was received on 02 Mar 2018, accepted on 24 May 2018 and first published on 05 Jun 2018


Article type: Paper
DOI: 10.1039/C8NJ01039K
Citation: New J. Chem., 2018, Advance Article
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    Controlling the polymerization of coniferyl alcohol with cyclodextrins

    L. Tarrago, C. Modolo, M. Yemloul, V. Robert, P. Rousselot-Pailley and T. Tron, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ01039K

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