Journal
CHEMICAL COMMUNICATIONS
Volume 54, Issue 100, Pages 14089-14092Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8cc08533a
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Funding
- Natural Science Foundation of China [21803030]
- Fundamental Research Funds for the Central Universities
- National Thousand Young Talents Program
- Jiangsu Specially-Appointed Professor Plan
- NSF of Jiangsu Province in China [BK20170631]
- National Institute of General Medical Sciences, National Institutes of Health [R01 GM109078]
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Sulfonamide derivatives have been used in pharmaceutics for decades. Here we report a new approach to release sulfonamides efficiently using a bioorthogonal reaction of sulfonyl sydnonimines and dibenzoazacyclooctyne (DIBAC). The second-order rate constant of the cycloaddition reaction can be up to 0.62 M-1 s(-1), and the reactants are highly stable under physiological conditions. Most significantly, we also discovered the mutual orthogonality between the sydnonimine-DIBAC and benzonorbornadiene-tetrazine cycloaddition pairs, which can be used for selective and simultaneous liberation of sulfonamide and primary amine drugs.
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