Work

Bioorthogonal Retro-Cope Elimination Reaction of N,N-Dialkylhydroxylamines and Strained Alkynes

Year: 2021

Type: article

Abstract: A bioorthogonal reaction between N, N -dialkylhydroxylamines and cyclooctynes is described. This reaction features a highly regioselective transformation between small, easily functionalizable reaction components with second-order rate constants reaching 84 M –1 s –1 . The reaction is orthogonal to the inverse-electron demand Diels–Alder reactions between tetrazine and strained alkenes, and its components exhibit exquisite stability and chemoselectivity in cell lysate. This retro-Cope elimination reaction introduces a new member to the bioorthogonal reaction compendium outside the prolific class of cycloaddition reactions.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.1c00885

Authors: Dahye Kang, Justin Kim

Institutions: Harvard University, Dana-Farber Cancer Institute

Language: English

Topic: Click Chemistry and Applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of Environmental Health Sciences

Award: Post-Translational Modification of Protein Surfaces