Synthesis and structural analysis of a β-hairpin peptide containing a sugar amino acid

B. Aguilera, G. Siegal, H.S. Overkleeft, N.J. Meeuwenoord, F.P.J.T. Rutjes, J.C.M. Hest, van, H.E. Schoemaker, G.A. van der Marel, J.H. van Boom, M. Overhand

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

The solid-phase synthesis of the linear peptide II (Ac-KKYTVSI-SAA2-KKITVSI) containing the novel sugar amino acid SAA2 [(2S,3S,6R)-6-aminomethyl-3-hydroxytetrahydro-pyran-2-carboxylic acid] is described. Structural analysis by NMR and CD in 50% aqueous methanol indicates that peptide II adopts a β-hairpin conformation, as reported earlier for the non-modified peptide I (Ac-KKYTVSINGKKITVSI).

Original languageEnglish
Pages (from-to)1541-1547
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number8
Publication statusPublished - 2001
Externally publishedYes

Keywords

  • β-Hairpin
  • β-Turn
  • Peptide isosters
  • Peptides
  • Sugar amino acids

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