Work

Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity

Year: 2008

Type: article

Abstract: Described is a bioorthogonal reaction that proceeds with unusually fast reaction rates without need for catalysis: the cycloaddition of s-tetrazine and trans-cyclooctene derivatives. The reactions tolerate a broad range of functionality and proceed in high yield in organic solvents, water, cell media, or cell lysate. The rate of the ligation between trans-cyclooctene and 3,6-di-(2-pyridyl)-s-tetrazine is very rapid (k2 2000 M-1 s-1). This fast reactivity enables protein modification at low concentration.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja8053805

Authors: Melissa L. Blackman, Maksim Royzen, Joseph M. Fox

Institution: University of Delaware

Language: English

Topic: Click Chemistry and Applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G630711813, SELECTIVE METHODS FOR SYNTHESIS WITH STRAINED MOLECULES AND CARBENOIDS