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

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

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)
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Abstract

The catalyst-free room temperature iClick reaction of an unsymmetrically 2,3-disubstituted oxanorbornadiene (OND) as a "masked" alkyne equivalent with [Mn(N3)(bpy(CH3,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.
Original languageEnglish
Pages (from-to)15692-15695
JournalChemical Communications
Volume50
Issue number99
DOIs
Publication statusPublished - 23 Oct 2014

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