Bioorthogonal Self-Immolative Linker Based on Grob Fragmentation.

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Authors
Ferhati, Xhenti
Salas-Cubero, Marina
  Garrido, Pablo
  García-Sanmartín, Josune
Guerreiro, Ana
Avenoza, Alberto
  Busto, Jesús H
Publication Date
2021-11-05
Journal Title
Org Lett
ISSN
1523-7060
Publisher
American Chemical Society (ACS)
Volume
23
Issue
21
Pages
8580-8584
Language
eng
Type
Article
This Version
VoR
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Citation
Ferhati, X., Salas-Cubero, M., Garrido, P., García-Sanmartín, J., Guerreiro, A., Avenoza, A., Busto, J. H., et al. (2021). Bioorthogonal Self-Immolative Linker Based on Grob Fragmentation.. Org Lett, 23 (21), 8580-8584. https://doi.org/10.1021/acs.orglett.1c03299
Abstract
A self-immolative bioorthogonal conditionally cleavable linker based on Grob fragmentation is described. It is derived from 1,3-aminocyclohexanols and allows the release of sulfonate-containing compounds in aqueous media. Modulation of the amine pKa promotes fragmentation even at slightly acidic pH, a common feature of several tumor environments. The Grob fragmentation can also occur under physiological conditions in living cells, highlighting the potential bioorthogonal applicability of this reaction.
Sponsorship
European Commission Horizon 2020 (H2020) Marie Sk?odowska-Curie actions (675007)
Identifiers
PMC8576835, 34694118
External DOI: https://doi.org/10.1021/acs.orglett.1c03299
This record's URL: https://www.repository.cam.ac.uk/handle/1810/332164
Rights
Attribution 4.0 International
Licence URL: https://creativecommons.org/licenses/by/4.0/
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Attribution 4.0 International
Except where otherwise noted, this item's licence is described as Attribution 4.0 International