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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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Authors
Henry, L.
Schneider, C.
Mützel, B.
Simpson, Peter
Nagel, C.
Fucke, K.
Schatzschneider, U.
Date
2014
Type
Journal Article

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Henry, L. and Schneider, C. and Mützel, B. and Simpson, P. and Nagel, C. and Fucke, K. and 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): pp. 15692-15695.
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Chemical Communications
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Nanochemistry Research Institute
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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.