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Comparison of boron-assisted oxime and hydrazone formations leads to the discovery of a fluorogenic variant

Stress, Cedric and Schmidt, Pascal and Gillingham, Dennis. (2016) Comparison of boron-assisted oxime and hydrazone formations leads to the discovery of a fluorogenic variant. Organic & Biomolecular Chemistry, 14. pp. 5529-5533.

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Abstract

We use kinetic data, photophysical properties, and mechanistic analyses to compare recently developed high-rate constant oxime and hydrazone formations. We show that when Schiff base formation between aldehydes and arylhydrazines is carried out with an appropriately positioned boron atom, then aromatic B–N heterocycles form irreversibly. These consist of an extended aromatic structure amenable to the tailoring of specific properties such as reaction rate and fluorescence. The reactions work best in neutral aqueous buffer and can be designed to be fluorogenic – properties which are particularly interesting in bioconjugation.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Organische Chemie (Gillingham)
UniBasel Contributors:Gillingham, Dennis
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Royal Society of Chemistry
ISSN:1477-0520
e-ISSN:1477-0539
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
Identification Number:
Last Modified:27 Feb 2017 13:07
Deposited On:27 Feb 2017 13:07

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