Isomeric triazines exhibit unique profiles of bioorthogonal reactivity

Autor:	David N Kamber, Jeffrey S Briggs, Sean S Nguyen, R. David Row, Hui-Wen Shih, Zane G Long, Fang Liu, K. N. Houk, Jennifer A. Prescher, Yong Liang
Rok vydání:	2019
Předmět:	Steric effects chemistry.chemical_classification 010405 organic chemistry Chemistry Alkyne General Chemistry 010402 general chemistry Biocompatible material 01 natural sciences Combinatorial chemistry Cycloaddition 0104 chemical sciences Reactivity (chemistry) Bioorthogonal chemistry
Zdroj:	Chemical Science
ISSN:	2041-6520
Popis:	Isomeric triazines can be tuned to exhibit unique reaction profiles with biocompatible strained alkenes and alkynes. 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::11b55943f3cb08d1015e95c9a481cb3f https://pubmed.ncbi.nlm.nih.gov/31908754 Zobrazit plný text záznamu