Synthesis of caged peptides using caged lysine: application to the synthesis of caged AIP, a highly specific inhibitor of calmodulin-dependent protein kinase II.
N(alpha)-Fmoc-N(epsilon)-(2-nitrobenzyloxycarbonyl)-lysine has been prepared and used in the solid-phase synthesis of caged peptides. The synthesized caged AIP (cagedKcagedKALRRQEAVDAL) showed characteristics required for caged peptides including a significantly reduced inhibitory activity to calmodulin-dependent protein kinase II and instantaneous recovery of the activity with photo-irradiation.
D054732:Calcium-Calmodulin-Dependent Protein Kinase Type 2; D017871:Calcium-Calmodulin-Dependent Protein Kinases / Q000037:antagonists & inhibitors*; D008239:Lysine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000493:pharmacokinetics; D009578:Nitrobenzenes / Q000138:chemical synthesis* / Q000493:pharmacokinetics*; D010452:Peptide Biosynthesis