Issue 39, 2018

Azlactone-based heterobifunctional linkers with orthogonal clickable groups: efficient tools for bioconjugation with complete atom economy

Abstract

We report the efficient synthesis of a series of new azlactone-based heterofunctional linkers bearing two orthogonal clickable groups that proceed with full atom economy. These new linkers comprise an azlactone (oxazolone) group that quickly reacts with amino groups in biologically relevant medium without byproduct elimination and a (bio)orthogonal handle which further undergoes facile and selective click reactions such as thiol–ene coupling, Diels–Alder or azide–alkyne cycloadditions. As an example, the application of this methodology to lysozyme PEGylation in aqueous medium is described.

Graphical abstract: Azlactone-based heterobifunctional linkers with orthogonal clickable groups: efficient tools for bioconjugation with complete atom economy

Supplementary files

Article information

Article type
Communication
Submitted
26 Jul 2018
Accepted
19 Sep 2018
First published
19 Sep 2018

Org. Biomol. Chem., 2018,16, 7124-7128

Azlactone-based heterobifunctional linkers with orthogonal clickable groups: efficient tools for bioconjugation with complete atom economy

H. T. Ho, A. Bénard, G. Forcher, M. Le Bohec, V. Montembault, S. Pascual and L. Fontaine, Org. Biomol. Chem., 2018, 16, 7124 DOI: 10.1039/C8OB01807C

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