Copper-free dual labeling of DNA by triazines and cyclopropenes as minimal orthogonal and bioorthogonal functions

Ulrike Reisacher, Damian Ploschik, Franziska Rönicke, Gergely B. Cserép, Péter Kele, Hans Achim Wagenknecht

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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.

Original languageEnglish
Pages (from-to)4032-4037
Number of pages6
JournalChemical Science
Issue number14
Publication statusPublished - Apr 14 2019


ASJC Scopus subject areas

  • Chemistry(all)

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