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Issue 14, 2019
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Copper-free dual labeling of DNA by triazines and cyclopropenes as minimal orthogonal and bioorthogonal functions

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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.

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

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Supplementary files

Article information


Submitted
14 Dec 2018
Accepted
01 Mar 2019
First published
04 Mar 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 4032-4037
Article type
Edge Article

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

U. Reisacher, D. Ploschik, F. Rönicke, G. B. Cserép, P. Kele and H. Wagenknecht, Chem. Sci., 2019, 10, 4032
DOI: 10.1039/C8SC05588B

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