Chemical synthesis of phosphopeptides using the arylthio group for protection of phosphate: application to identification of cdc2 kinase phosphorylation sites.
Synthesis of two O-phosphorylated dipeptides, N-Boc-O[S,S-bis(p-methoxyphenyl)phosphorodithioyl] -serylproline and N-Boc-O-[S,S-bis(p-methoxyphenyl) phosphorodithioyl]threonylproline, as new O-phosphorylated dipeptide building blocks for the synthesis of O-phosphorylated peptides, is described. Peptides containing phosphoserine or phosphothreonine were prepared by use of these building blocks in the Boc mode of liquid-phase peptide synthesis. Sites phosphorylated by cdc2 kinase were easily identified using these chemically synthesized phosphopeptides.
Ueno
Y
Y
Department of Life Chemistry, Tokyo Institute of Technology, Yokohama, Japan.
Makino
S
S
Kitagawa
M
M
Nishimura
S
S
Taya
Y
Y
Hata
T
T
D000595:Amino Acid Sequence; D001665:Binding Sites; D016203:CDC2 Protein Kinase / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D010748:Phosphopeptides / Q000138:chemical synthesis*; D010766:Phosphorylation; D010768:Phosphoserine / Q000737:chemistry*; D010769:Phosphothreonine / Q000737:chemistry*; D016160:Retinoblastoma Protein / Q000378:metabolism
D010748:Phosphopeptides; D016160:Retinoblastoma Protein; D010769:Phosphothreonine; D010768:Phosphoserine; D016203:CDC2 Protein Kinase