Issue 87, 2016

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

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

Supplementary files

Article information

Article type
Communication
Submitted
13 Sep 2016
Accepted
07 Oct 2016
First published
14 Oct 2016
This article is Open Access
Creative Commons BY license

Chem. Commun., 2016,52, 12901-12904

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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