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Synthesis and polymerisation of maleoyl-L-histidine monomers and addition of histidine to an ethylene-alt-maleic co-polymer

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Abstract

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] 20D  = −11) than the monomer ([α] 20D  = +25), which is ascribed to the threo-diisotactic and/or threo-disyndiotactic stereoregularity of the polymer.

Grafting and polymerisation of maleoyl-L-histidine monomers

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Acknowledgments

The authors are grateful to Mr. Anders Mårtensson for valuable discussions regarding vibrational spectra and to Dr. Anders Höije for aid during the SEC-MALLS measurements. The Foundation for Strategic Environmental Research, MISTRA, is acknowledged for financial support.

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Authors and Affiliations

  1. Applied Surface Chemistry, Department of Chemical and Biological Engineering, Chalmers University of Technology, SE-412 96, Gothenburg, Sweden

    Markus Andersson Trojer & Magnus Nydén

  2. I-Tech AB, SE-413 14, Gothenburg, Sweden

    Dan Isaksson

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  1. Markus Andersson Trojer
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  2. Dan Isaksson
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Correspondence to Markus Andersson Trojer.

Electronic supplementary material

The online version of this article [doi:10.1007/s10965-012-9821-9] contains supplementary materials, comprising NMR spectra and FTIR vibrational spectra of monomers and polymers, which is available to authorised users.

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Trojer, M.A., Isaksson, D. & Nydén, M. Synthesis and polymerisation of maleoyl-L-histidine monomers and addition of histidine to an ethylene-alt-maleic co-polymer. J Polym Res 19, 9821 (2012). https://doi.org/10.1007/s10965-012-9821-9

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