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Synthesis 2000; 2000(5): 707-713
DOI: 10.1055/s-2000-6388
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3′-C-Branched Thymidine 5′-Triphosphates: Synthesis, Application, and Coupling with Near-Infrared Oxazine Fluorescent Dye

Thomas Schoetzau* , Ulrich Koert, Joachim W. Engels
  • *Fachbereich Chemie der Humboldt-Universität, Hessische Str. 1-2, 10115 Berlin, Germany
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Publication Date:
31 December 2000 (online)

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The synthesis of the novel class of 3′-C-modified thymidine nucleotides is described. The aldehyde 1 was converted into the derivatives 5, 7, and 10 that differ in the length of the carbon chain. One-pot phosphorylation gave the corresponding triphosphates 11, 12, 13. The 3′-C-(2-azidoethyl)-3′-deoxythymidine 5′-triphosphate 13 was reduced by triphenylphosphine to the amino nucleotide 14. All amino nucleotides have been dye-labelled at the aliphatic amino group with the oxazine dye JA242. All triphosphates were tested as terminators in DNA-sequencing reactions.

3′-C-modified nucleoside - dideoxynucleoside 5′-triphosphates - dye labelling - radical reaction