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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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 52; no. 31; pp. 5451 - 5454
Main Authors Tian, He, Sakmar, Thomas P, Huber, Thomas
Format Journal Article
LanguageEnglish
Published England 01.01.2016
Subjects
Alkynes - chemistry
Animals
Azides - chemistry
Cattle
Cycloaddition Reaction
Cyclooctanes - chemistry
Cysteine
Cysteine - chemistry
Labels
Medicin och hälsovetenskap
Mercaptoethanol - chemistry
Models, Molecular
Photoreceptors
Preserving
Reagents
Rhodopsin - chemistry
Strategy
Sulfhydryl Compounds - chemistry
Utilities
Visual
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/c6cc01321j