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

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.

SUBMITTER: Reisacher U

PROVIDER: S-EPMC6450502 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Copper-free dual labeling of DNA by triazines and cyclopropenes as minimal orthogonal <i>and</i> bioorthogonal functions.

Reisacher Ulrike U Ploschik Damian D Rönicke Franziska F Cserép Gergely B GB Kele Péter P Wagenknecht Hans-Achim HA

Chemical science 20190304 14

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 ...[more]

PMID: 31015943

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