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End-Group Characterization of Poly(O-benzyl-L-tyrosine) by NALDI-TOF MS...

by Deanna L Pickel, Jamie M Messman, Nikolaos Politakos, Apostolos Avgeropoulos
Publication Type
Conference Paper
Publication Date
Conference Name
237th ACS National Meeting & Exposition
Conference Location
Salt Lake City, Utah, United States of America
Conference Sponsor
American Chemical Society
Conference Date
-

The primary amine initiated polymerization of N-carboxyanhydrides of amino acids (NCAs) has been proposed to proceed by two mechanisms: normal amine mechanism and activated monomer mechanism. Recently, Hadjichristidis <i>et al.</i> showed that high vacuum techniques could be employed to synthesize poly(amino acid)s initiated with primary amines exclusively <i>via</i> the normal amine mechanism. Unfortunately, no end group characterization was reported. Herein we report the end group characterization of the amine-initiated polymerization of the NCA of O-benzyl-L-tyrosine by MALDI-TOF MS and NALDI <sup>TM</sup>-TOF MS. We show that when synthesized <i>via</i> high vacuum techniques the reaction proceeds exclusively by the normal amine mechanism. The activated monomer mechanism is detected in samples prepared by less rigorous techniques.