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Issue 31, 2016
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A simple method for enhancing the bioorthogonality of cyclooctyne reagent

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Abstract

The cross-reactivity between some cyclooctynes and thiols limits the bioorthogonality of the strain-promoted azide–alkyne cycloaddition reaction. We show that a low concentration of β-mercaptoethanol significantly reduces the undesirable side reaction between bicyclononyne (BCN) and cysteine and while preserving free cysteines. We site-specifically label a genetically-encoded azido group in the visual photoreceptor rhodopsin to demonstrate the utility of the strategy.

Graphical abstract: A simple method for enhancing the bioorthogonality of cyclooctyne reagent

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Article information


Submitted
12 Feb 2016
Accepted
18 Mar 2016
First published
18 Mar 2016

Chem. Commun., 2016,52, 5451-5454
Article type
Communication
Author version available

A simple method for enhancing the bioorthogonality of cyclooctyne reagent

H. Tian, T. P. Sakmar and T. Huber, Chem. Commun., 2016, 52, 5451
DOI: 10.1039/C6CC01321J

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