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Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a MnI(bpy)(CO)3-coordinated azide

Henry, Lucas; Schneider, Christoph; Muetzel, Benedict; Simpson, Peter V.; Nagel, Christoph; Fucke, Katharina; Schatzschneider, Ulrich

Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a MnI(bpy)(CO)3-coordinated azide Thumbnail


Authors

Lucas Henry

Christoph Schneider

Benedict Muetzel

Peter V. Simpson

Christoph Nagel

Katharina Fucke

Ulrich Schatzschneider



Contributors

K Edkins (nee Fucke) kdht75@durham.ac.uk
Other

Abstract

The catalyst-free room temperature iClick reaction of an unsymmetrically 2,3-disubstituted oxanorbornadiene (OND) as a “masked” alkyne equivalent with [Mn(N3)(bpyCH3,CH3)(CO)3] leads to isolation of a phenylalanine ester bioconjugate, in which the model amino acid is linked to the metal moiety via a N-2-coordinated triazolate formed in a cycloaddition-retro-Diels–Alder (crDA) reaction sequence, in a novel approach to bioorthogonal coupling reactions based on metal-centered reactivity.

Citation

Henry, L., Schneider, C., Muetzel, B., Simpson, P. V., Nagel, C., Fucke, K., & Schatzschneider, U. (2014). Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a MnI(bpy)(CO)3-coordinated azide. Chemical Communications, 50(99), 15692-15695. https://doi.org/10.1039/c4cc07892f

Journal Article Type Article
Publication Date Dec 25, 2014
Deposit Date Dec 16, 2014
Publicly Available Date Dec 17, 2014
Journal Chemical Communications
Print ISSN 1359-7345
Electronic ISSN 1364-548X
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 50
Issue 99
Pages 15692-15695
DOI https://doi.org/10.1039/c4cc07892f

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