Mechanistic Insight in the Enzymatic Ring-Opening Polymerization of beta-Propiolactam

Here we report the polymerization of beta-propiolactam to poly(beta-alanine) catalyzed by the immobilized Candida antarctica lipase B (N435). The polymer is characterized by (1)H-NMR spectroscopy and MALDI-ToF mass spectrometry. The best results were obtained with N435 (dried for 24 hours in vacua a...

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Bibliographic Details
Main Authors: Schwab, Leendert W., Baum, Iris, Fels, Gregor, Loos, Katja
Other Authors: Cheng, HN, Gross, RA
Format: Article in Journal/Newspaper
Language:English
Published: AMER CHEMICAL SOC 2010
Subjects:
ANTARCTICA LIPASE-B
CANDIDA-ANTARCTICA
EPSILON-CAPROLACTONE
ORGANIC-SOLVENTS
AMINO ACIDS
LACTAMS
SPECIFICITY
Antarc*
Antarctica
Online Access:https://hdl.handle.net/11370/c33dd882-2f8a-4dc9-b5c3-f22ab9221730
https://research.rug.nl/en/publications/c33dd882-2f8a-4dc9-b5c3-f22ab9221730
Description
Summary:Here we report the polymerization of beta-propiolactam to poly(beta-alanine) catalyzed by the immobilized Candida antarctica lipase B (N435). The polymer is characterized by (1)H-NMR spectroscopy and MALDI-ToF mass spectrometry. The best results were obtained with N435 (dried for 24 hours in vacua at 46 degrees C) in toluene at 55 degrees C for a period of 96 hours. Polymerization of beta-alanine was not feasible via the N435 catalyst, showing that the beta-propiolactam ring is needed for this reaction. This finding ruled out reaction mechanisms that resembled enzymatic polymerization of epsilon-caprolactone. Instead, a detailed eight-step mechanism was developed by computational simulation that provided an appropriate description of ring-opening polymerization of beta-propiolactam.

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