Open AccessPolyisocyanides 5 . Synthesis and polymerization of carbylhistidine and carbylhistamine
Author(s) -
van der Eijk J. M.,
Nolte R. J. M.,
Drenth W.
Publication year - 1978
Publication title -
recueil des travaux chimiques des pays‐bas
Language(s) - English
Resource type - Journals
ISSN - 0165-0513
DOI - 10.1002/recl.19780970206
Subject(s) - imidazole , polymerization , trifluoroacetic acid , chemistry , histidine , polymer chemistry , chloride , histamine , nickel , isocyanide , polymer , methanol , organic chemistry , medicine , enzyme
Polymer anchored imidazole functions were obtained by polymerization of carbylhistidine and carbylhistamine. These isocyanides were synthesized from L ‐histidine and histamine, respectively. In order to obtain the former isocyanide in optically active form, it was necessary to work at low basicity and to prevent temperatures higher than ambient. Polymerization occurred with 1 mol % nickel chloride and a small amount of trifluoroacetic acid in methanol. The poly(carbylhistidine) showed no optical activity. The apparent p K a of the imidazole function in poly(carbylhistamine) has decreased to 5.2 ± 0.1 compared with free imidazole (7.2), whereas it rises to 9.4 ± 0.2 in poly(carbylhistidine).
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