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Phthalimide: a potential warhead for switchable and bioorthogonal conjugation
Kosuke Chiba1,2, Takumi Yoshida1, Kana Okada1
1Graduate School of Pharmaceutical Sciences, The University of Osaka, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. obika@phs.osaka-u.ac.jp.
Abstract:
4-Azidophthalimide, previously reported as a photoaffinity labeling (PAL) tag, was repurposed as a post-conjugation warhead. Using the phthalimide-amine reaction, cyanine amines were successfully conjugated to target proteins after PAL and later replaced with other amines, demonstrating its "switchable" nature. These findings highlight phthalimide's unique characteristics as a novel chemical tool for bioorthogonal conjugations.
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