Issue 14, 2018

Controlling the polymerization of coniferyl alcohol with cyclodextrins

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

Supplementary files

Article information

Article type
Paper
Submitted
02 Mar 2018
Accepted
24 May 2018
First published
05 Jun 2018

New J. Chem., 2018,42, 11770-11775

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, 42, 11770 DOI: 10.1039/C8NJ01039K

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