Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 50, Pages 22514-22522Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202010217
Keywords
bioconjugation; cysteine; photocatalysis; photosensitizers; thiol-ene click chemistry
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Funding
- Institute for Basic Science [IBS-R010-A2]
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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 photosensitizerQ(PEG)can be used for visible-light-induced cysteine-specific bioconjugation for the installation ofQ(PEG)by exploiting its intrinsic photosensitizing ability to activate the S-H bond of cysteine. The slightly modifiedQ(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.
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