General method for the synthesis of caged phosphopeptides: tools for the exploration of signal transduction pathways.
[reaction: see text] An interassembly approach for the synthesis of peptides containing 1-(2-nitrophenyl)ethyl-caged phosphoserine, -threonine, and -tyrosine has been developed. Photochemical uncaging of these peptides releases the 2-nitrophenylethyl protecting group to afford the corresponding phosphopeptide. The peptides described herein are based on phosphorylation sites of kinases involved in cell movement or cell cycle regulation and demonstrate the versatility of the method and compatibility with the synthesis of polypeptides, including a variety of encoded amino acids.
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.
Deborah M
DM
Rothman
M Eugenio
ME
Vázquez
Elizabeth M
EM
Vogel
Barbara
B
Imperiali
D010455:Peptides / Q000138:chemical synthesis*; D010766:Phosphorylation; D010768:Phosphoserine / Q000138:chemical synthesis; D010769:Phosphothreonine / Q000138:chemical synthesis; D019000:Phosphotyrosine / Q000138:chemical synthesis; D010782:Photolysis; D015398:Signal Transduction
D010455:Peptides; D010769:Phosphothreonine; D010768:Phosphoserine; D019000:Phosphotyrosine