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A simple method for enhancing the bioorthogonality of cyclooctyne reagent.

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.

SUBMITTER: Tian H 

PROVIDER: S-EPMC4824645 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

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A simple method for enhancing the bioorthogonality of cyclooctyne reagent.

Tian He H   Sakmar Thomas P TP   Huber Thomas T  

Chemical communications (Cambridge, England) 20160401 31

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. ...[more]

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