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Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. Univ Massachusetts Lowell, USA.
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2017 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 40, p. 12117-12121Article in journal (Refereed) Published
Abstract [en]

We report a fast Staudinger reaction between perfluoroaryl azides (PFAAs) and aryl phosphines, which occurs readily under ambient conditions. A rate constant as high as 18m(-1)s(-1) was obtained between methyl 4-azido-2,3,5,6-tetrafluorobenzoate and methyl 2-(diphenylphosphanyl)benzoate in CD3CN/D2O. Furthermore, the iminophosphorane product was stable toward hydrolysis and aza-phosphonium ylide reactions. This PFAA Staudinger reaction proved to be an excellent bioothorgonal reaction. PFAA-derivatized mannosamine and galactosamine were successfully transformed into cell-surface glycans and efficiently labeled with phosphine-derivatized fluorophore-conjugated bovine serum albumin.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2017. Vol. 56, no 40, p. 12117-12121
Keyword [en]
bioconjugation, bioorthogonal reactions, metabolic labelling, perfluoroaryl azides, Staudinger reaction
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-215444DOI: 10.1002/anie.201705346ISI: 000411267800010PubMedID: 28796447OAI: oai:DiVA.org:kth-215444DiVA, id: diva2:1150703
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QC 20171019

Available from: 2017-10-19 Created: 2017-10-19 Last updated: 2017-10-19Bibliographically approved

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Ramström, OlofYan, Mingdi

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