A new practical strategy for the synthesis of long-chain phosphopeptide.
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.
Miyoshi
K
K
Graduate School of Pharmaceutical Sciences, Kyoto University, Japan.
Otaka
A
A
Kaneko
M
M
Tamamura
H
H
Fujii
N
N
D000595:Amino Acid Sequence; D004952:Esters; D008969:Molecular Sequence Data; D010748:Phosphopeptides / Q000138:chemical synthesis* / Q000737:chemistry
D004952:Esters; D010748:Phosphopeptides