Incorporation of primary amines into a poly(1,5-dioxepan-2-one) via lipase-catalyzed ring-opening polymerization

A simple chemo-enzymatic strategy for the synthesis of functionalized poly(1,5-dioxepane-2-one)esters has been developed. The protocol involves first the reaction of a primary amine with 1,5-dioxepane-2-one (2) to give an amide carrying a terminal primary hydroxyl group, followed by an enzymatic ring-opening polymerization catalyzed by Novozym 435. The proposed method is easy to handle and is suitable for the incorporation of different amines, as it has been shown with the model benzyl amine (3), the functionalized amines tyramine (4) and propargylamine (5), and the bioactive compound N-deacetylthiocolchicine (6).