Synthesis and polymerisation of maleolyl-L-histidine monomers and addition of histidine to an ethylene-alt-maleic co-polymer
Artikel i vetenskaplig tidskrift, 2012

This work has investigated two routes of synthesising polymers containing L-histidine using maleimide chemistry; grafting of histidine onto an ethylene-alt-maleic anhydride copolymer and AIBN (azobisisobutyronitrile) initiated radical polymerisation of the monomer maleoyl-L-histidine. The grafting technique and monomer synthesis are utilising the maleimide formation between the primary amine of histidine and maleic anhydride. The reactions are conveniently carried out in one step with good yields. The copolymers containing L-histidine were prepared by reacting L-histidine or L-histidine methyl ester with poly(ethylene-alt maleic anhydride) in DMSO at 50 °C for 8–16 h with 80% yields independent of the degree of substitution. The monomer maleoyl-L-histidine was synthesised by reacting histidine and maleic anhydride in acetic acid and the monomer was subsequently polymerised by AIBN radical initiation in DMSO at 80 °C for 48 h to yield poly(N-histidyl maleimide). The resulting polymer had a different optical rotation ([α]D20 = −11) than the monomer ([α]D20 = +25), which is ascribed to the threo-diisotactic and/or threo-disyndiotactic stereoregularity of the polymer.

Histidine – Maleimide – Maleic anhydride – Radical polymerisation – Post-polymerisation modification

Författare

Markus Andersson Trojer

SuMo Biomaterials

Chalmers, Kemi- och bioteknik, Teknisk ytkemi

Dan Isaksson

I-Tech AB

Magnus Nydén

Chalmers, Kemi- och bioteknik, Teknisk ytkemi

SuMo Biomaterials

Journal of Polymer Research

1022-9760 (ISSN) 1572-8935 (eISSN)

Vol. 19 9821-9829

Ämneskategorier

Polymerkemi

Organisk kemi

Fundament

Grundläggande vetenskaper

Drivkrafter

Innovation och entreprenörskap

Styrkeområden

Materialvetenskap

DOI

10.1007/s10965-012-9821-9