Site-specific DNA labelling by Staudinger ligation

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2011
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Walker, John
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MARK, Sonny S., ed.. Bioconjugation Protocols. Totowa, NJ: Humana Press, 2011, pp. 195-207. Methods in Molecular Biology. 751. ISBN 978-1-61779-150-5. Available under: doi: 10.1007/978-1-61779-151-2_12
Zusammenfassung

Site-specific and chemoselective labeling of DNA is still a difficult task. The Staudinger ligation is a bioorthogonal reaction between azides and phosphines that requires no catalyst to proceed, allowing for mild reaction conditions. The reaction may be extended for site-specific labeling of DNA using azidomodified triphosphates, which can be incorporated site-specifically into DNA strands by DNA polymerases in a template-dependent manner. The azido-modified DNA, in turn, can be labeled by suitable phosphines. This protocol describes (1) the synthesis of an azido-TTP analogue; (2) the enzymatic synthesis of azido-modified DNA; (3) the synthesis of suitable phosphine labels; and (4) the labeling of azido-DNA with biotin–phosphine by Staudinger ligation with approximately 70% conversion.

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540 Chemie
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Site-specific DNA labeling, DNA modification, Staudinger ligation, Phosphine, Modified triphosphate, Azido thymidine, DNA polymerase, Azido-DNA, Biotin
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ISO 690WEISBROD, Samuel H., Anna BACCARO, Andreas MARX, WALKER, John, ed., 2011. Site-specific DNA labelling by Staudinger ligation. In: MARK, Sonny S., ed.. Bioconjugation Protocols. Totowa, NJ: Humana Press, 2011, pp. 195-207. Methods in Molecular Biology. 751. ISBN 978-1-61779-150-5. Available under: doi: 10.1007/978-1-61779-151-2_12
BibTex
@incollection{Weisbrod2011Sites-14013,
  year={2011},
  doi={10.1007/978-1-61779-151-2_12},
  title={Site-specific DNA labelling by Staudinger ligation},
  number={751},
  isbn={978-1-61779-150-5},
  publisher={Humana Press},
  address={Totowa, NJ},
  series={Methods in Molecular Biology},
  booktitle={Bioconjugation Protocols},
  pages={195--207},
  editor={Mark, Sonny S.},
  author={Weisbrod, Samuel H. and Baccaro, Anna and Marx, Andreas}
}
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    <dcterms:abstract xml:lang="eng">Site-specific and chemoselective labeling of DNA is still a difficult task. The Staudinger ligation is a bioorthogonal reaction between azides and phosphines that requires no catalyst to proceed, allowing for mild reaction conditions. The reaction may be extended for site-specific labeling of DNA using azidomodified triphosphates, which can be incorporated site-specifically into DNA strands by DNA polymerases in a template-dependent manner. The azido-modified DNA, in turn, can be labeled by suitable phosphines. This protocol describes (1) the synthesis of an azido-TTP analogue; (2) the enzymatic synthesis of azido-modified DNA; (3) the synthesis of suitable phosphine labels; and (4) the labeling of azido-DNA with biotin–phosphine by Staudinger ligation with approximately 70% conversion.</dcterms:abstract>
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