Alkene–Tetrazine Ligation for Imaging Cellular DNA1. Issue 35 (30th June 2014)

• Record Type: Journal Article
• Authors: Rieder, Ulrike; Luedtke, Nathan W.
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 35(2014)
• Page Start: 9168
• Page End: 9172
• Publication Date: 2014-06-30
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201403580
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 (<italic>k</italic>≈0.02 <sc>M</sc>⁻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.</p> </abstract>