Here we report the polymerization of �-propiolactam to poly(�-alanine) catalyzed by the immobilized Candida antarctica lipase B (N435). The polymer is characterized by 1H-NMR spectroscopy and MALDI-ToF mass spectrometry. The best results were obtained with N435 (dried for 24 hours in vacuo at 46 �C) in toluene at 55 �C for a period of 96 hours. Polymerization of �-alanine was not feasible via the N435 catalyst, showing that the �-propiolactam ring is needed for  this reaction.  This finding ruled out reaction mechanisms that resembled enzymatic polymerization of e-caprolactone. Instead, a detailed eight-step mechanism was developed by computational simulation that provided an appropriate description of ring-opening polymerization of �-propiolactam.

Enzymatic polymerization of poly-β-alanine: Establishing the reaction mechanism

243rd National Meeting (2012)

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