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Issue 99, 2014
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Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a MnI(bpy)(CO)3-coordinated azide

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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)(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.

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

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Article information


Submitted
06 Oct 2014
Accepted
23 Oct 2014
First published
23 Oct 2014

Chem. Commun., 2014,50, 15692-15695
Article type
Communication

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

L. Henry, C. Schneider, B. Mützel, P. V. Simpson, C. Nagel, K. Fucke and U. Schatzschneider, Chem. Commun., 2014, 50, 15692
DOI: 10.1039/C4CC07892F

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