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In Macromol. Rapid Commun.: Different Routes to Polydehydroalanine

Polydehydroalanine (PDha) is a polyampholyte featuring both a -NH2 and a -COOH in every repeat unit and with that presents a rather high charge density. We herein report on the synthesis and polymerization of two monomers, benzyl 2-tert-bu­toxy­carbonyl­aminoacrylate (tBABA) and methyl 2-benzyloxy­carbonyl­amino­acrylate (BOMA), which feature different protective groups and, after polymerization, the resulting PtBABA and PBOMA can be trans­formed into PDha using polymer-analogous modification reactions. More important, the current choice of protective groups allows either simultaneous deprotection in one step in both cases, but also the orthogonal deprotection of either -NH2 or -COOH moiety for PtBABA, given that appropriate conditions are chosen. The polymers have been prepared using free radical polymerization and all (intermediate) polymeric materials have been investigated using a combination of NMR spectroscopy and size exclusion chromatography (SEC).

Original Article:

J. Kruse, P. Biehl, F. H. Schacher, "Different Routes to Ampholytic Polydehydroalanine - Orthogonal vs. Simultaneous Deprotection", Macromol. Rapid Commun. 2019, in press


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