Solid-phase synthesis of "mixed" peptidomimetics using Fmoc-protected aza-beta3-amino acids and alpha-amino acids.
[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.
Busnel
Olivier
O
Groupe Ciblage et Auto-Assemblages Fonctionnels, UMR CNRS 6510, Institut de Chimie, Université de Rennes I, Av. du Général Leclerc, F-35042 Rennes Cédex, France.
Bi
Lanrong
L
Dali
Hayet
H
Cheguillaume
Arnaud
A
Chevance
Soizic
S
Bondon
Arnaud
A
Muller
Sylviane
S
Baudy-Floc'h
Michèle
M
D000596:Amino Acids / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
D000596:Amino Acids; D005449:Fluorenes; D010455:Peptides