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Chem Commun (Camb). 2016 Apr 7;52(31):5451-4. doi: 10.1039/c6cc01321j.

A simple method for enhancing the bioorthogonality of cyclooctyne reagent.

Author information

1
Laboratory of Chemical Biology and Signal Transduction, The Rockefeller University, 1230 York Ave., New York, NY 10065, USA. sakmar@rockefeller.edu hubert@rockefeller.edu.
2
Laboratory of Chemical Biology and Signal Transduction, The Rockefeller University, 1230 York Ave., New York, NY 10065, USA. sakmar@rockefeller.edu hubert@rockefeller.edu and Department of Neurobiology, Care Sciences and Society, Division for Neurogeriatrics, Center for Alzheimer Research, Karolinska Institutet, 141 57 Huddinge, Sweden.

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.

PMID:
27009873
PMCID:
PMC4824645
DOI:
10.1039/c6cc01321j
[Indexed for MEDLINE]
Free PMC Article

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