Development of caged non-hydrolyzable phosphoamino acids and application to photo-control of binding affinity of phosphopeptide mimetic to phosphopeptide-recognizing protein.
The design and synthesis of caged non-hydrolyzable phospho-serine, -threonine, and -tyrosine derivatives that generate parent non-hydrolyzable phosphoamino acids, containing a difluoromethylene unit instead of the oxygen of a phosphoester, after UV-irradiation are described. The caged non-hydrolyzable amino acids were incorporated into peptides by standard Fmoc solid-phase peptide synthesis, and the obtained peptides were successfully converted to the parent non-hydrolyzable phosphopeptides by UV-irradiation. Application of the caged non-hydrolyzable phosphoserine-containing peptide to photo-control the binding affinity of the peptide to 14-3-3β protein is also reported.
Institute of Health Biosciences and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505, Japan.
Koji
K
Ebisuno
Institute of Health Biosciences and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505, Japan.
Masaya
M
Denda
Institute of Health Biosciences and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505, Japan.
Keiji
K
Ogura
Institute of Health Biosciences and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505, Japan.
Tsubasa
T
Inokuma
Institute of Health Biosciences and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505, Japan. Electronic address: shigenaga.akira@tokushima-u.ac.jp.
Akira
A
Shigenaga
Institute of Health Biosciences and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi, Tokushima 770-8505, Japan. Electronic address: aotaka@tokushima-u.ac.jp.
Akira
A
Otaka
D048948:14-3-3 Proteins / Q000737:chemistry*; D019606:Phosphoamino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D010748:Phosphopeptides / Q000737:chemistry*; D055668:Photochemical Processes; D014466:Ultraviolet Rays
D048948:14-3-3 Proteins; D019606:Phosphoamino Acids; D010748:Phosphopeptides
Caged peptide; Non-hydrolyzable; Phosphoamino acid; Phosphopeptide; UV-responsive