title: Solid-phase synthesis of peptides containing the spin-labeled 2,2,6,6-tetramethylpiperidine-1-oxyl-4-amino-4-carboxylic acid (TOAC).
abstract: 2,2,6,6-Tetramethylpiperidine-1-oxyl-4-amino4-carboxylic acid (TOAC) is a nitroxide spin-labeled, achiral Calpha-tetrasubstituted amino acid recently shown to be not only an effective beta-turn and 3(10)/alpha-helix promoter in peptides, but also an excellent rigid electron paramagnetic resonance probe and fluorescence quencher. Here, we demonstrate that TOAC can be effectively incorporated into internal positions of peptide sequences using Fmoc chemistry and solid-phase synthesis in an automated apparatus.
authors.affiliation: Department of Protein Engineering, Commissariat à l'Energie Atomique, Gif-sur-Yvette, France.
authors.forename: L
authors.initials: L
authors.lastname: Martin
authors.forename: A
authors.initials: A
authors.lastname: Ivancich
authors.forename: C
authors.initials: C
authors.lastname: Vita
authors.forename: F
authors.initials: F
authors.lastname: Formaggio
authors.forename: C
authors.initials: C
authors.lastname: Toniolo
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D003497:Cyclic N-Oxides / Q000737:chemistry* / Q000494:pharmacology; D004578:Electron Spin Resonance Spectroscopy; D013058:Mass Spectrometry; D008956:Models, Chemical; D010452:Peptide Biosynthesis; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013113:Spin Labels; D013997:Time Factors
chemical_list: D000596:Amino Acids; D003497:Cyclic N-Oxides; D010455:Peptides; D013113:Spin Labels; C037109:2,2,6,6-tetramethylpiperidine-N-oxide-4-amino-4-carboxylic acid