A simple method for enhancing the bioorthogonality of cyclooctyne reagent

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 whi...

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Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2016-04, Vol.52 (31), p.5451-5454
Hauptverfasser:	Tian, He, Sakmar, Thomas P, Huber, Thomas
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkynes - chemistry Animals Azides - chemistry beta-mercaptoethanol Cattle cross reaction Cycloaddition Reaction cycloaddition reactions Cyclooctanes - chemistry Cysteine Cysteine - chemistry Labels Mercaptoethanol - chemistry Models, Molecular Photoreceptors Preserving Reagents rhodopsin Rhodopsin - chemistry Strategy Sulfhydryl Compounds - chemistry thiols Utilities Visual
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Beschreibung
Zusammenfassung:	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.
ISSN:	1359-7345 1364-548X 1364-548X
DOI:	10.1039/c6cc01321j