Strain-promoted cycloadditions involving nitrones and alkynes--rapid tunable reactions for bioorthogonal labeling

Douglas A MacKenzie; Allison R Sherratt; Mariya Chigrinova; Lawrence L W Cheung; John Paul Pezacki

doi:10.1016/j.cbpa.2014.05.023

Strain-promoted cycloadditions involving nitrones and alkynes--rapid tunable reactions for bioorthogonal labeling

Curr Opin Chem Biol. 2014 Aug:21:81-8. doi: 10.1016/j.cbpa.2014.05.023. Epub 2014 Jul 11.

Authors

Douglas A MacKenzie¹, Allison R Sherratt², Mariya Chigrinova¹, Lawrence L W Cheung¹, John Paul Pezacki³

Affiliations

¹ Life Sciences Division, National Research Council of Canada, Ottawa, Ontario, Canada; Department of Chemistry, University of Ottawa, Ottawa, Canada.
² Life Sciences Division, National Research Council of Canada, Ottawa, Ontario, Canada.
³ Life Sciences Division, National Research Council of Canada, Ottawa, Ontario, Canada; Department of Chemistry, University of Ottawa, Ottawa, Canada. Electronic address: john.pezacki@nrc-cnrc.gc.ca.

PMID: 25022431
DOI: 10.1016/j.cbpa.2014.05.023

Abstract

The development and applications of strain-promoted alkyne-nitrone cycloaddition (SPANC) reactions have brought about new tools for rapid and specific functionalization of biomolecules in different settings. While a number of strain-promoted reactions have been successfully developed, SPANC reactions offer high reactivity with bimolecular rate constants of k2 that are as fast as 60M(-1)s(-1). SPANC reactions also offer stability of starting materials, particularly in the case of endocyclic nitrones, as well as stereoelectronic tunability of the nitrone moiety to optimize reactivity towards different alkyne reaction partners. Herein we discuss recent advances in the development of SPANC reactions and their applications in bioorthogonal labeling.

Publication types

Review

MeSH terms

Alkynes / chemistry*
Cycloaddition Reaction / methods*
Kinetics
Nitrogen Oxides / chemistry*
Staining and Labeling / methods*

Substances

Alkynes
Nitrogen Oxides
nitrones