Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a MnI(bpy)(CO)3-coordinated azide
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چکیده
منابع مشابه
Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a Mn(I)(bpy)(CO)3-coordinated azide.
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 sequenc...
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The copper-catalyzed azide-alkyne cycloaddition reaction is widely used for the connection of molecular entities of all sizes. A protocol is provided here for the process with biomolecules. Ascorbate is used as reducing agent to maintain the required cuprous oxidation state. Since these convenient conditions produce reactive oxygen species, five equivalents of a copper-binding ligand is used wi...
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Since its discovery in 2002, the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction—the most widely recognized example of click chemistry—has been rapidly embraced for applications in myriad fields. The attractiveness of this procedure (and its copper-free strained-alkyne variant) stems from the selective reactivity of azides and alkynes only with each other. Because of the fragile na...
متن کاملSite-Specific Bioconjugation of a Murine Dihydrofolate Reductase Enzyme by Copper(I)-Catalyzed Azide-Alkyne Cycloaddition with Retained Activity
Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) is an efficient reaction linking an azido and an alkynyl group in the presence of copper catalyst. Incorporation of a non-natural amino acid (NAA) containing either an azido or an alkynyl group into a protein allows site-specific bioconjugation in mild conditions via CuAAC. Despite its great potential, bioconjugation of an enzyme has been hampe...
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ژورنال
عنوان ژورنال: Chem. Commun.
سال: 2014
ISSN: 1359-7345,1364-548X
DOI: 10.1039/c4cc07892f