Orthogonal, metal-free surface modification by strain-promoted azide–alkyne and nitrile oxide–alkene/alkyne cycloadditions
نویسندگان
چکیده
منابع مشابه
Solid phase strain promoted "click" modification of DNA via [3+2]-nitrile oxide-cyclooctyne cycloadditions.
Rapid, catalyst free, solid phase modification of DNA by strain promoted cyclooctyne-nitrile oxide click chemistry is reported; the reaction is characterised by mild conditions, occurring in an aqueous environment under atmospheric conditions at room temperature and is complete in 10 minutes.
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Strain promoted cycloaddition is presented as a tool for RNA conjugation on the solid phase; RNA-cyclooctyne conjugates are prepared by cycloaddition to both azide (strain-promoted azide-alkyne cycloaddition, SPAAC) and nitrile oxide dipoles (strain-promoted nitrile oxide-alkyne cycloaddition, SPNOAC). The conjugation is compatible with 2'-OMe blocks and with 2'-O-TBDMS protection on the ribose...
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The bioorthogonal chemical reporter strategy is emerging as a versatile method for the labeling of biomolecules, such as nucleic acids, lipids, carbohydrates, and proteins. In this approach, an abiotic chemical functionality (reporter) is incorporated into a target biomolecule and can then react with a complementary bioorthogonal functional group linked to one of a diverse set of probes. The az...
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Strain-promoted oxidation-controlled cyclooctyne-1,2-quinone cycloaddition (SPOCQ) between functionalized bicyclo[6.1.0]non-4-yne (BCN) and surface-bound quinones revealed an unprecedented 100 % conjugation efficiency. In addition, monitoring by direct analysis in real time mass spectrometry (DART-MS) revealed the underlying kinetics and activation parameters of this immobilization process in d...
متن کاملNitrones as dipoles for rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes.
Strain-promoted cycloadditions of nitrones with cyclooctynes (k(2) = 1.5 M(-1) s(-1) at 25 degrees C) are up to 25 times more rapid than comparable reactions of azides.
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ژورنال
عنوان ژورنال: Chemical Science
سال: 2012
ISSN: 2041-6520,2041-6539
DOI: 10.1039/c2sc20555f