Synthesis of C8-arylamine-modified 2'-deoxyadenosine phosphoramidites and their site-specific incorporation into oligonucleotides

Szombati, Zita; Baerns, Sabrina; Marx, Andreas; Meier, Chris

Synthesis of C8-arylamine-modified 2'-deoxyadenosine phosphoramidites and their site-specific incorporation into oligonucleotides

Dateien

Marx_synthesis_phosphoramidites.pdfGröße: 7.58 MBDownloads: 519

Datum

2012

Autor:innen

Szombati, Zita

Baerns, Sabrina

Marx, Andreas

Meier, Chris

Open Access-Veröffentlichung

Open Access Green

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

ChemBioChem. 2012, 13(5), pp. 700-712. ISSN 1439-4227. eISSN 1439-7633. Available under: doi: 10.1002/cbic.201100573

Zusammenfassung

Adducts of C8-(N-acetyl)-arylamines and 2’-deoxyadenosine were synthesised by palladium-catalysed C N cross-coupling chemistry. These 2’-dA adducts were converted into the corresponding 3’-phosphoramidites and site-specifically incorporated into DNA oligonucleotides, which were characterised by mass spectrometry, UV thermal-stability assays and circular dichroism. These modified oligonucleotides were also used in EcoRI restriction assays and in primer-extension studies with three different DNA polymerases. The incorporation of the 2’-dA lesion close to the EcoRI restriction site dramatically reduced the susceptibility of the DNA strand to cleavage; this indicates a significant local distortion of the DNA double helix. The incorporation of the acetylated C8-2’-dA-phosphoramidites into 20-mer oligonucleotides failed, however, because the Nacetyl group was lost during the deprotection process. Instead the corresponding C8-NH-2’-dA-modified oligonucleotides were obtained. The effect of the C8-NH-arylamine-dA lesion on the replication by DNA polymerases was clearly dependent both on the polymerase used and on the arylamine-dA damage.

Fachgebiet (DDC)

540 Chemie

Zitieren

ISO 690

SZOMBATI, Zita, Sabrina BAERNS, Andreas MARX, Chris MEIER, 2012. Synthesis of C8-arylamine-modified 2'-deoxyadenosine phosphoramidites and their site-specific incorporation into oligonucleotides. In: ChemBioChem. 2012, 13(5), pp. 700-712. ISSN 1439-4227. eISSN 1439-7633. Available under: doi: 10.1002/cbic.201100573

BibTex

@article{Szombati2012-03-19Synth-18845,
  year={2012},
  doi={10.1002/cbic.201100573},
  title={Synthesis of C8-arylamine-modified 2'-deoxyadenosine phosphoramidites and their site-specific incorporation into oligonucleotides},
  number={5},
  volume={13},
  issn={1439-4227},
  journal={ChemBioChem},
  pages={700--712},
  author={Szombati, Zita and Baerns, Sabrina and Marx, Andreas and Meier, Chris}
}

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    <dcterms:abstract xml:lang="eng">Adducts of C8-(N-acetyl)-arylamines and 2’-deoxyadenosine were synthesised by palladium-catalysed C N cross-coupling chemistry. These 2’-dA adducts were converted into the corresponding 3’-phosphoramidites and site-specifically incorporated into DNA oligonucleotides, which were characterised by mass spectrometry, UV thermal-stability assays and circular dichroism. These modified oligonucleotides were also used in EcoRI restriction assays and in primer-extension studies with three different DNA polymerases. The incorporation of the 2’-dA lesion close to the EcoRI restriction site dramatically reduced the susceptibility of the DNA strand to cleavage; this indicates a significant local distortion of the DNA double helix. The incorporation of the acetylated C8-2’-dA-phosphoramidites into 20-mer oligonucleotides failed, however, because the Nacetyl group was lost during the deprotection process. Instead the corresponding C8-NH-2’-dA-modified oligonucleotides were obtained. The effect of the C8-NH-arylamine-dA lesion on the replication by DNA polymerases was clearly dependent both on the polymerase used and on the arylamine-dA damage.</dcterms:abstract>
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