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Cyclic peptides containing a δ-sugar amino acid—synthesis and evaluation as artificial receptors

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Author

Summary, in English

An Fmoc-protected δ-sugar amino acid, prepared by oxidation of a glucosamine derivative, was coupled to three different tripeptide tert-butyl esters (H-Tyr-Tyr-Tyr-OtBu, H-Tyr-Glu(OBzl)-Tyr-OtBu and H-Tyr-Arg(Mtr)-Tyr-OtBu) and the resulting sugar amino acid/amino acid hybrids were transformed into dimers that were subsequently cyclized to give three C2-symmetric macrocycles. The macrocycles were deprotected and their binding properties towards p-nitrophenyl glycosides, nucleotides, and purines were examined. Of the ligands screened, only some of the purines showed weak, but significant, binding.

Publishing year

2005

Language

English

Pages

863-874

Publication/Series

Tetrahedron

Volume

61

Issue

4

Document type

Journal article

Publisher

Elsevier

Topic

  • Organic Chemistry

Keywords

  • artificial receptors
  • cyclic peptides
  • sugar amino acids
  • macrocycles
  • molecular recognition

Status

Published

ISBN/ISSN/Other

  • ISSN: 0040-4020