Chemoenzymatic Synthesis of Fluorescent and Colored Polyesters

• Published in: ChemCatChem 2011-02, Vol.3 (2), p.331-337
• Main Authors: Navarra, Cristina, Marzorati, Mattia, Danieli, Bruno, Riva, Sergio
• Format: Article
• Language: English
• Subjects: biocatalysis; fluorescence; lipases; polymers; ring-opening polymerization
• ISSN: 1867-3880; 1867-3899
• DOI: 10.1002/cctc.201000327

A simple chemoenzymatic strategy for the synthesis of colored and fluorescent poly(ε‐caprolactone) esters has been developed. The procedure involves first the reaction of a functionalized primary amine with ε‐caprolactone, to give an amide with a terminal primary hydroxy 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 shown for the yellow compound N‐deacetylthiocolchicine and the fluorescent amines 4‐(2‐aminoethylamino)‐7‐(N,N‐dimethylsulfamoyl)benzofurazan and dansylcadaverine. A similar strategy is considered for the synthesis of poly(ε‐caprolactone) esters, employing alcohols as initiators of the reaction. In this case, an intermediate ester carrying a terminal primary hydroxy group cannot be isolated and the reaction forms directly the desired polymers. A glowing concern: A simple chemoenzymatic strategy for the synthesis of colored and fluorescent poly(ε‐caprolactone) esters has been developed, involving the reaction of a functionalized primary amine with ε‐caprolactone, to give an amide with a terminal primary hydroxy group, followed by an enzymatic ring‐opening polymerization catalyzed by Novozym 435. The method is easy to handle and suitable for the incorporation of different amines.