CAL-B catalyzed regioselective bulk polymerization of l-aspartic acid diethyl ester to α-linked polypeptides?

Chemical Communications Pub Date: 2017-03-17 DOI: 10.1039/C7CC01300K

Abstract

This paper reports that the bulk polymerization of L-aspartic acid diethyl ester catalyzed by immobilized CAL-B at 80 °C for 24 h gives primarily (～95%) α-linked poly(L-aspartate) in 70% yield with DPavg = 50 and regioselectivity (α/β) = 94?:?6. Plots of log{[M]0/[M]t} vs. time and DPavgvs. conversion indicate that this polymerization proceeds in a controlled manner by a chain-growth mechanism up to 90% conversion. Thereafter, competition occurs between chain growth and step mechanisms.

Graphical abstract: CAL-B catalyzed regioselective bulk polymerization of l-aspartic acid diethyl ester to α-linked polypeptides
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