Issue 39, 2019

Isomeric triazines exhibit unique profiles of bioorthogonal reactivity

Abstract

Expanding the scope of bioorthogonal reactivity requires access to new and mutually compatible reagents. We report here that 1,2,4-triazines can be tuned to exhibit unique reaction profiles with biocompatible strained alkenes and alkynes. Computational analyses were used to identify candidate orthogonal reactions, and the predictions were experimentally verified. Notably, 5-substituted triazines, unlike their 6-substituted counterparts, undergo rapid [4 + 2] cycloadditions with a sterically encumbered strained alkyne. This unique, sterically controlled reactivity was exploited for dual bioorthogonal labeling. Mutually orthogonal triazines and cycloaddition chemistries will enable new multi-component imaging applications.

Graphical abstract: Isomeric triazines exhibit unique profiles of bioorthogonal reactivity

Supplementary files

Article information

Article type
Edge Article
Submitted
22 mar 2019
Accepted
11 aug 2019
First published
21 aug 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 9109-9114

Isomeric triazines exhibit unique profiles of bioorthogonal reactivity

D. N. Kamber, S. S. Nguyen, F. Liu, J. S. Briggs, H. Shih, R. D. Row, Z. G. Long, K. N. Houk, Y. Liang and J. A. Prescher, Chem. Sci., 2019, 10, 9109 DOI: 10.1039/C9SC01427F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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