Solid-phase synthesis of "mixed" peptidomimetics using Fmoc-protected aza-beta3-amino acids and alpha-amino acids

J Org Chem. 2005 Dec 23;70(26):10701-8. doi: 10.1021/jo051585o.

Abstract

[structure: see text] A solid-phase fluorenylmethyloxycarbonyl (Fmoc)-based synthesis strategy is described for "mixed" aza-beta3-peptides as well as a convenient general approach for their required building blocks, the aza-beta3-amino acid residues (aza-beta3-aa). These monomers allow the synthesis of relatively large quantities of pure mixed aza-beta3-peptides. The required Fmoc-substituted aza-beta3-amino acids are accessible by convenient synthesis, and a number of monomers including those containing side chains with functional groups have been synthesized. The method was applied toward the solid-phase synthesis of aza-beta3-peptide mimetics of a biologically active histone H4 sequence.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Fluorenes / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Mimicry*
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Amino Acids
  • Fluorenes
  • Peptides