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

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
• Public URL: https://durham-repository.worktribe.com/output/1415262