SI 1 Electronic Supplementary Information Luminogenic “Clickable” Lanthanide Complexes for Protein Labeling. Nicolas Candelon, Niculina D. Hădade,* Mihaela Matache, Jean-Louis Canet, Federico Cisnetti, Daniel P. Funeriu,* Lionel Nauton, and Arnaud Gautier* SI 1-Synthesis and characterization of ligands and ABPs 2 1.1 General remarks 2 1.2 Synthesis of the ligands. 2 1.3 Determination of the molecular weight of 2aH 2 x TFA and 2bH 4 x TFA 4 1.4 Synthesis of activity-based probes 5, 6. 4 1.5 RP-HPLC chromatograms of 5 and 6. 6 SI 2- NMR study of yttrium(III) complexes 7 SI 3- Luminescence measurements 12 3.1 Instrumental parameters 12 3.2 Preparation of lanthanide(III) complexes solutions 12 3.3 Additional luminescence spectra 13 3.4 Speciation diagram for Eu-dpa 14 3.5 Luminescence decays 15 3.6 Determination of the metal–bound water molecules number 20 3.7 Quantum yield determination 22 3.8 Kinetic survey of the formation of [Tb(2c)] - 25 SI 4- Preparative BSA labeling 26 4.1 BSA labeling procedure with BCN 26 4.2 MALDI-TOF-MS analysis of the BCN-BSA conjugate 26 SI 5- Papain Labeling 27 5.1 General procedure for lanthanide complexation of peptide 6 and papain-6 conjugate 27 5.2 General procedure for the reaction between papain and peptide 5, peptide 6 or lanthanide complexes of 6. 27 5.3 General procedure for CuAAC between ligand 1aH 2 (or complexes [Ln(1a) 3 ] 3– ) and the alkyne-modified papain (papain-5 conjugate). 27 5.4 Sensitivity for papain detection 27 5.5 Labeling of papain in E. Coli BL21 cell lysates. 28 Electronic Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2013