Copper-free dual labeling of DNA by triazines and cyclopropenes as minimal orthogonal and bioorthogonal functions. Issue 14 (11th March 2019)

• Record Type: Journal Article
• Authors: Reisacher, Ulrike; Ploschik, Damian; Rönicke, Franziska; Cserép, Gergely B.; Kele, Péter; Wagenknecht, Hans-Achim
• Is Part Of: Chemical science. Volume 10:Issue 14(2019)
• Page Start: 4032
• Page End: 4037
• Publication Date: 2019-03-11
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c8sc05588b
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Two different and small functions for inverse electron demand Diels–Alder reactions were applied for dual labeling of DNA: the 1, 2, 4-triazine was attached to the 5-position of 2′-deoxyuridine, and the 1-methylcyclopropene to the 7-position of 7-deaza-2′-deoxyadenosine. Abstract : Two different and small functions for inverse electron demand Diels–Alder reactions were applied for dual labeling of DNA: the 1, 2, 4-triazine was attached to the 5-position of 2′-deoxyuridine triphosphate, and the 1-methylcyclopropene to the 7-position of 7-deaza-2′-deoxyadenosine triphosphate. These two modified nucleotides were sequence-selectively incorporated into oligonucleotides by DNA polymerases. These products were labeled by two different fluorescent dyes using postsynthetic reactions that are not only bioorthogonal in general, but also mutually orthogonal.