Silicon Chemistry

, Volume 1, Issue 3, pp 215-222

First online:

Amino acid and peptide chemistry on silicones

  • Frank J. LaRondeAffiliated withDepartment of Chemistry, McMaster University
  • , Michael A. BrookAffiliated withDepartment of Chemistry, McMaster University
  • , Gang HuAffiliated withDepartment of Chemistry, McMaster University

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Poly(dimethylsiloxanes), di-terminated with amino acids, were synthesized by employing the Diels-Alder reaction of cyclopentadiene- or furan-terminated poly(dimethylsiloxanes) with functional dienophiles including N-maleoyl-protected phenylalanine. The amino acid could be chain extended using conventional solution peptide coupling with DCC, DMAP and N-hydroxysuccinimide to give a dipeptide-terminated silicone. The molecular weight of the silicone component of the telechelic system could be increased by acid-catalyzed redistribution with octamethylcyclotetrasiloxane (D4).

functional silicones amino acids peptides