Enzyme-Catalyzed Ring-Opening polymerization of ε-caprolactone using Alkyne Functionalized Initiators

 

Marcela Castano1,   Jukuan Zheng1,   Judit E. Puskas1,2 and  Matthew L. Becker1 

1 Department of Polymer Science, The University of Akron, Akron, OH 44325-3909, USA

2 Department of Chemical and Biomolecular Engineering, The University of Akron, Akron, OH 44325-3906, USA

 

Well-​defined poly(caprolactone)​s were generated using alkyne-​based initiating systems catalyzed by Candida antarctica Lipase B (CALB)​.  Propargyl alc. and 4-​dibenzocyclooctynol (DIBO) were shown to efficiently initiate the polymns. under metal free conditions and yielded 4 to 24 KDa polymers with relatively narrow mol. mass distribution.  The alkyne bonds in the strained and unstrained initiating systems survived the polymn. conditions and the purifn. process.  The resulting bonds can be sequentially functionalized post-​polymn. using metal free and copper catalyzed click chem. conditions.

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