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Visible‐Light‐Induced Cysteine‐Specific Bioconjugation: Biocompatible Thiol–Ene Click Chemistry
Author(s) -
Choi Hangyeol,
Kim Myojeong,
Jang Jaebong,
Hong Sungwoo
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202010217
Subject(s) - bioconjugation , cysteine , biomolecule , chemistry , combinatorial chemistry , photosensitizer , biocompatible material , thiol , peg ratio , click chemistry , reactivity (psychology) , photochemistry , biochemistry , enzyme , medicine , biomedical engineering , alternative medicine , finance , pathology , economics
Bioconjugation methods using visible‐light photocatalysis have emerged as powerful synthetic tools for the selective modification of biomolecules under mild reaction conditions. However, the number of photochemical transformations that allow successful protein bioconjugation is still limited because of the need for stringent reaction conditions. Herein, we report that a newly developed water‐compatible fluorescent photosensitizer Q PEG can be used for visible‐light‐induced cysteine‐specific bioconjugation for the installation of Q PEG by exploiting its intrinsic photosensitizing ability to activate the S−H bond of cysteine. The slightly modified Q CAT enables the effective photocatalytic cysteine‐specific conjugation of biologically relevant groups. The superior reactivity and cysteine selectivity of this methodology was further corroborated by traceless bioconjugation with a series of complex peptides and proteins under biocompatible conditions.