@-Tide-stabilized beta-hairpins

J Org Chem. 2005 Mar 4;70(5):1865-71. doi: 10.1021/jo047782p.

Abstract

As minimalist versions of beta-structure, two-stranded beta-hairpins are commonly employed as platforms for assessing the interactions that stabilize beta-sheets in proteins. We have found that the presence of a 1,6-dihydro-3(2H)-pyridinone moiety (the "@-unit") as an amino acid replacement at the i - 1 or i + 4 positions relative to a beta-turn strongly stabilizes the hairpin conformation. Hybrids of this type bridge the gap between natural beta-hairpins and unnatural beta-sheets because the @-unit only replaces one residue in a peptide while stabilizing the hairpin conformation to a greater extent than a normal amino acid. In this report, we describe the synthesis of a variety of @-tide-templated hairpins and the NMR and CD characterization of their conformations in both polar and nonpolar solvents.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Hydrogen Bonding
  • Macromolecular Substances / chemistry
  • Peptides / chemistry*
  • Protein Conformation*
  • Protein Structure, Secondary*
  • Pyridones / chemistry*

Substances

  • Macromolecular Substances
  • Peptides
  • Pyridones