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Tyrosine-Selective Bioconjugation with Iminoxyl Radicals
preprintsubmitted on 10.05.2020, 12:15 and posted on 12.05.2020, 10:22 by Katsuya Maruyama, Takashi Ishiyama, Yohei Seki, Kounosuke Oisaki, Motomu Kanai
A novel Tyr-selective protein bioconjugation using the water-soluble persistent iminoxyl radical is described. The conjugation proceeded with high Tyr-selectivity and short reaction time under biocompatible conditions (room temperature in buffered media under air). The stability of the conjugates was tunable depending on the steric hindrance of iminoxyl. The presence of sodium ascorbate and/or light irradiation promoted traceless deconjugation, restoring the native Tyr structure. The method is applied to the synthesis of a protein-dye conjugate and further derivatization to azobenzene-modified peptides.