title: A safety catch linker for Fmoc-based assembly of constrained cyclic peptides.
abstract: A new safety-catch linker for Fmoc solid-phase peptide synthesis of cyclic peptides is reported. The linear precursors were assembled on a tert-butyl protected catechol derivative using optimized conditions for Fmoc-removal. After activation of the linker using TFA, neutralization of the N-terminal amine induced cyclization with concomitant cleavage from the resin yielding the cyclic peptides in DMF solution. Several constrained cyclic peptides were synthesized in excellent yields and purities.
authors.affiliation: Institute for Molecular Bioscience, University of Queensland, St Lucia, Qld 4072, Australia.
authors.forename: Jacob
authors.initials: J
authors.lastname: Ravn
authors.forename: Gregory T
authors.initials: GT
authors.lastname: Bourne
authors.forename: Mark L
authors.initials: ML
authors.lastname: Smythe
mesh_terms: D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques; D005449:Fluorenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010456:Peptides, Cyclic / Q000737:chemistry*
chemical_list: D005449:Fluorenes; D010456:Peptides, Cyclic