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Amino acid and peptide chemistry on silicones

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Silicon Chemistry

Abstract

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).

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Authors and Affiliations

  1. Department of Chemistry, McMaster University, 1280 Main St. W., Hamilton, Ontario, Canada, L8S 4M1

    Frank J. LaRonde, Michael A. Brook & Gang Hu

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  1. Frank J. LaRonde
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  2. Michael A. Brook
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  3. Gang Hu
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LaRonde, F.J., Brook, M.A. & Hu, G. Amino acid and peptide chemistry on silicones. Silicon Chemistry 1, 215–222 (2002). https://doi.org/10.1023/A:1021290121661

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