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Incorporation of Primary Amines into a Polyester Chain by a Combination of Chemical and Lipase‐Catalyzed ε‐Caprolactone Ring‐Opening Processes
Author(s) -
Marzorati Mattia,
Hult Karl,
Riva Sergio,
Danieli Bruno
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600642
Subject(s) - chemistry , polyester , amine gas treating , benzylamine , tryptamine , primary (astronomy) , amide , lipase , caprolactone , catalysis , organic chemistry , chemical modification , combinatorial chemistry , polymer chemistry , enzyme , copolymer , polymer , biochemistry , physics , astronomy
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 ε‐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 .