Synlett 2001; 2001(2): 0210-0213
DOI: 10.1055/s-2001-10779
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Solid-Phase Synthesis of a Novel Peptide Substituted Calix[4]arene

Suzanne Beckham Shuker* , Julie Esterbrook, Jose Gonzalez
  • *School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta Georgia 30332-0400; Fax 404 894-2295; E-mail: suzy.shuker§chemistry.gatech.edu
Further Information

Publication History

Publication Date:
31 December 2001 (online)

The described approach provides calix[4]arene scaffolds that can be coupled to amino acids using standard solid phase peptide synthesis, providing a route for the rapid preparation of combinatorial libraries of this class of molecular hosts. In addition, we report the first example of a tetrapeptido-calix[4]arene in which the amino acids are attached to the upper rim through the carboxy termini. Specifically, a tetra-nitrocalix[4]arene was prepared, attached to solid support, and the nitro groups were reduced to the corresponding amines by treatment with SnCl2 · H2O. This was followed by three successive couplings with alanine to provide the tetra(trialanine)calix[4]arene. The final product was cleaved from the solid support and shown by LCMS to elute as one peak with the expected mass.

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