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

Johan Billing, Ulf Nilsson

Research output: Contribution to journalArticlepeer-review

41 Citations (SciVal)

Abstract

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.
Original languageEnglish
Pages (from-to)863-874
JournalTetrahedron
Volume61
Issue number4
DOIs
Publication statusPublished - 2005

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

  • Organic Chemistry

Keywords

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

Fingerprint

Dive into the research topics of 'Cyclic peptides containing a δ-sugar amino acid—synthesis and evaluation as artificial receptors'. Together they form a unique fingerprint.

Cite this