title: Solid-phase synthesis of phenylalanine containing peptides using a traceless triazene linker.
abstract: The use of a triazene function to anchor phenylalanine to a polymeric support through its side chain is reported. To prove the usefulness of this strategy in solid-phase peptide synthesis, several bioactive peptides have been prepared including cyclic, C-modified, and protected peptides. The triazene linkage is formed by coupling the diazonium salt of Fmoc-Phe(pNH(2))-OAllyl to a MBHA-polystyrene resin previously functionalized with isonipecotic acid (90%). Further assembly of the peptide chain, cleavage from the resin using 2-5% TFA in DCM, and reduction of the resulting diazonium salt of the peptide with FeSO(4)·7H(2)O in DMF afforded the desired products in high purities (73-94%).
authors.affiliation: Department of Organic Chemistry, University of Barcelona, Diagonal 647, 08028 Barcelona, Spain.
authors.forename: Carolina
authors.initials: C
authors.lastname: Torres-García
authors.forename: Daniel
authors.initials: D
authors.lastname: Pulido
authors.forename: Magdalena
authors.initials: M
authors.lastname: Carceller
authors.forename: Iván
authors.initials: I
authors.lastname: Ramos
authors.forename: Miriam
authors.initials: M
authors.lastname: Royo
authors.forename: Ernesto
authors.initials: E
authors.lastname: Nicolás
mesh_terms: D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D010649:Phenylalanine / Q000138:chemical synthesis* / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D014227:Triazines / Q000737:chemistry*
chemical_list: D010455:Peptides; D014227:Triazines; D010649:Phenylalanine