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Issue 87, 2016
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A ‘photorelease, catch and photorelease’ strategy for bioconjugation utilizing a p-hydroxyphenacyl group

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Abstract

A bioorthogonal ‘catch and photorelease’ strategy, which combines alkyne–azide cycloaddition between p-hydroxyphenacyl azide and alkyne derivatives to form a 1,2,3-triazole adduct and subsequent photochemical release of the triazole moiety via a photo-Favorskii rearrangement, is introduced. The first step can also involve photorelease of a strained alkyne and its Cu-free click reaction with azide.

Graphical abstract: A ‘photorelease, catch and photorelease’ strategy for bioconjugation utilizing a p-hydroxyphenacyl group

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Publication details

The article was received on 13 Sep 2016, accepted on 07 Oct 2016 and first published on 14 Oct 2016


Article type: Communication
DOI: 10.1039/C6CC07496K
Citation: Chem. Commun., 2016,52, 12901-12904
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    A ‘photorelease, catch and photorelease’ strategy for bioconjugation utilizing a p-hydroxyphenacyl group

    D. Madea, T. Slanina and P. Klán, Chem. Commun., 2016, 52, 12901
    DOI: 10.1039/C6CC07496K

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