Solution syntheses of two enkephalin-containing peptides, peptide E and dynorphin(1-24), using Nin-(2,4,6-triisopropylphenylsulfonyl)tryptophan.
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.
Kitagawa
K
K
Kawamoto
T
T
Futaki
S
S
Kiyama
S
S
Akita
T
T
Moritoki
H
H
Kiso
Y
Y
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
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