title: A new practical strategy for the synthesis of long-chain phosphopeptide.
abstract: A new practical strategy has been developed for the synthesis of long-chain phosphopeptide. Both the 2-chlorobenzyloxycarbonyl (CIZ) group for Lys and methyl (Me) for phosphoamino acids remained intact, while other commonly used side-chain protecting groups were cleaved quantitatively, during the reaction using a highly acidic trifluoromethanesulfonic acid (TFMSA)-based reagent system (High TFMSA: TFMSA-TFA-m-cresol=1:9:1, v/v). Selective deprotection of the CIZ and Me group-containing protected phosphopeptide resin with the High TFMSA gave a partially protected phosphopeptide fragment suitable for thioester-mediated fragment condensation. A deprotection protocol of the 9-fluorenylmethyloxycarbonyl (Fmoc) group, which evades significant side reaction toward the protected phosphoamino acid, was also developed. These two new findings enabled us to synthesize long-chain phosphopeptide via thioester-mediated fragment condensation.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Miyoshi
authors.forename: A
authors.initials: A
authors.lastname: Otaka
authors.forename: M
authors.initials: M
authors.lastname: Kaneko
authors.forename: H
authors.initials: H
authors.lastname: Tamamura
authors.forename: N
authors.initials: N
authors.lastname: Fujii
mesh_terms: D000595:Amino Acid Sequence; D004952:Esters; D008969:Molecular Sequence Data; D010748:Phosphopeptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004952:Esters; D010748:Phosphopeptides