title: Alkene-tetrazine ligation for imaging cellular DNA.
abstract: 5-Vinyl-2'-deoxyuridine (VdU) is the first reported metabolic probe for cellular DNA synthesis that can be visualized by using an inverse electron demand Diels-Alder reaction with a fluorescent tetrazine. VdU is incorporated by endogenous enzymes into the genomes of replicating cells, where it exhibits reduced genotoxicity compared to 5-ethynyl-2'-deoxyuridine (EdU). The VdU-tetrazine ligation reaction is rapid (k≈0.02 M(-1) s(-1)) and chemically orthogonal to the alkyne-azide "click" reaction of EdU-modified DNA. Alkene-tetrazine ligation reactions provide the first alternative to azide-alkyne click reactions for the bioorthogonal chemical labeling of nucleic acids in cells and facilitate time-resolved, multicolor labeling of DNA synthesis.
authors: Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich (Switzerland) http://www.bioorganic-chemistry.com.
authors: Ulrike
authors: U
authors: Rieder
authors: Nathan W
authors: NW
authors: Luedtke
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D057930:Click Chemistry; D004247:DNA / Q000032:analysis* / Q000138:chemical synthesis / Q000737:chemistry*; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D013777:Tetrazoles / Q000737:chemistry*
chemical_list: D000475:Alkenes; D013777:Tetrazoles; C011381:5-vinyl-2'-deoxyuridine; D004247:DNA; D003857:Deoxyuridine
keywords: Diels-Alder cycloaddition; bioorthogonal reporters; fluorescent probes; metabolic labeling; nucleosides