Incorportaion of primary amines into a polyester chain by a combination of chemical and lipase-catalyzed epsilon-caprolactone ring-opening processes

A simple chemoenzymatic strategy for the incorporation of bioactive and suitably functionalized molecules into a polyester chain has been developed. The protocol involves first the reaction of a primary amine with -caprolactone to give an amide carrying a terminal primary hydroxy group, followed by...

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Bibliographic Details
Published in:Advanced Synthesis & Catalysis
Main Authors: MARZORATI, MATTIA, B. Danieli, K. Hult, S. Riva
Other Authors: M. Marzorati
Format: Article in Journal/Newspaper
Language:English
Published: Wiley-VCH 2007
Subjects:
ε-caprolactone
Amine
Candida antarctica lipase
Enzyme catalysi
Novozym 435
Ringopening polymerization
Settore CHIM/06 - Chimica Organica
Antarc*
Antarctica
Online Access:http://hdl.handle.net/2434/42259
https://doi.org/10.1002/adsc.200600642
Description
Summary:A simple chemoenzymatic strategy for the incorporation of bioactive and suitably functionalized molecules into a polyester chain has been developed. The protocol involves first the reaction of a primary amine with -caprolactone to give an amide carrying a terminal primary hydroxy group, followed by the enzymatic growth of the polymeric chain triggered by Novozym 435. This method is versatile and easy to handle and is suitable for the incorporation of different amines into polyesters, as has been shown with the model compounds benzylamine and tryptamine, the bioactive compound N-deacetylthiocolchicine and the functionalized propargylamine and tyramine .

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