New Click on the Block: Photocaged Hydroxylamine, an Addition to the Light-Activatable Bioorthogonal Toolbox
- PMID: 40576186
- DOI: 10.1002/chem.202501721
New Click on the Block: Photocaged Hydroxylamine, an Addition to the Light-Activatable Bioorthogonal Toolbox
Abstract
A new photoactivatable bioorthogonal function was added to the photoactivatable bioorthogonal toolbox by transiently disabling the bioorthogonal reactivity of the hydroxylamine moiety with a photolabile protecting group. The photocaged bioorthogonal function was further equipped with a HaloTag substrate to enable its use in live-cell labeling schemes. Light-controlled recovery of reactivity was demonstrated by bioorthogonal fluorescent labeling of intracellular proteins in live cells.
Keywords: bioorthogonal; caged hydroxylamine; light activation; photocage; retro Cope ligation.
© 2025 The Author(s). Chemistry – A European Journal published by Wiley‐VCH GmbH.
References
-
- (a) R. E. Bird, S. A. Lemmel, X. Yu, Q. A. Zhou, Bioconjugate Chem. 2021, 32, 2457;
-
- (b) E. Kozma, P. Kele, Top. Curr. Chem. (Z) 2024, 382, 7.
-
- S. L. Scinto, D. A. Bilodeau, R. Hincapie, W. Lee, S. S. Nguyen, M. Xu, C. W. am Ende, M. G. Finn, K. Lang, Q. Lin, J. P. Pezacki, J. A. Prescher, M. S. Robillard, J. M. Fox, Nat. Rev. Methods Primers 2021, 1, 30.
-
- K. R. Venrooij, L. de Bondt, K. M. Bonger, Top. Curr. Chem. (Z) 2024, 382, 24.
-
- (a) M. Wilkovitsch, W. Kuba, P. Keppel, B. Sohr, A. Löffler, S. Kronister, A. F. del Castillo, M. Goldeck, R. Dzijak, M. Rahm, M. Vrabel, D. Svatunek, J. C. T. Carlson, H. Mikula, Angew. Chem. Int. Ed. 2025, 64, e202411707;
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
