title: Solution syntheses of two enkephalin-containing peptides, peptide E and dynorphin(1-24), using Nin-(2,4,6-triisopropylphenylsulfonyl)tryptophan.
abstract: Two enkephalin-containing peptides, peptide E and dynorphin(1-24), were synthesized by conventional solution methods employing a new Trp derivative, Nin-(2,4,6-triisopropylphenylsulfonyl)tryptophan [Trp(Tps)]. All protecting groups employed including the Tps group were removed by treatment with 1 M trifluoromethanesulfonic acid (TFMSA)-thioanisole in trifluoroacetic acid (TFA) at the final steps of these syntheses. Subsequent purifications by Sephadex G-25 chromatography, CM-Biogel A ion exchange chromatography, and reversed-phase high-performance liquid chromatography afforded highly purified samples. Both synthetic peptide E and dynorphin(1-24) exhibited high in vitro opioid activity. The usefulness of this new tryptophan derivative for practical peptide synthesis was established through these syntheses of complex Trp-containing peptides.
authors.forename: K
authors.initials: K
authors.lastname: Kitagawa
authors.forename: T
authors.initials: T
authors.lastname: Kawamoto
authors.forename: S
authors.initials: S
authors.lastname: Futaki
authors.forename: S
authors.initials: S
authors.lastname: Kiyama
authors.forename: T
authors.initials: T
authors.lastname: Akita
authors.forename: H
authors.initials: H
authors.lastname: Moritoki
authors.forename: Y
authors.initials: Y
authors.lastname: Kiso
mesh_terms: D000595:Amino Acid Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D004399:Dynorphins / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004745:Enkephalins; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D012996:Solutions; D014364:Tryptophan / Q000031:analogs & derivatives
chemical_list: D004745:Enkephalins; D007202:Indicators and Reagents; D010455:Peptides; D012996:Solutions; C062854:N-(2,4,6-triisopropylphenylsulfonyl)tryptophan; D004399:Dynorphins; C039933:peptide E (adrenal medulla); C062855:dynorphin (1-24); D014364:Tryptophan