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Primary Amine and Solvent‐Induced Polymerizations of L ‐ or D , L ‐Phenylalanine N ‐Carboxyanhydride
Author(s) -
Kricheldorf Hans R.,
v. Lossow Colin,
Schwarz Gert
Publication year - 2005
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200400417
Subject(s) - chemistry , polymer chemistry , polymerization , amine gas treating , phenylalanine , aniline , solvent , amide , organic chemistry , polymer , amino acid , biochemistry
Summary: Benzylamine, hexylamine and aniline‐initiated polymerizations of D , L ‐phenylalanine and L ‐phenylalanine N ‐carboxyanhydride ( D , L ‐Phe‐NCA and L ‐Phe‐NCA) were performed in various solvents. The isolated polypeptides were characterized by MALDI‐TOF mass spectroscopy. Exclusively linear polypeptides having one amide and one amino endgroup were found, when the polymerizations were conducted in a closed reaction vessel with dioxane or sulfolane as reaction media. Traces of water competed with aniline as initiator, when the reaction vessel was closed with a drying tube. In N , N ‐dimethylformamide (DMF) formyl endgroups were formed at polymerization temperatures of 60 °C. In DMF and N ‐methylpyrrolidone, cyclic oligo‐ and polypeptides were formed by a solvent‐induced polymerization initiated by zwitterions, which may compete with the primary amine‐initiated polymerizations.MALDI‐TOF mass spectrum of a poly( D , L ‐phenylalanine) polymerized in NMP without addition of an initiator.