Fluorescent labeling of (oligo)nucleotides by a new fluoride cleavable linker capable of versatile attachment modes

Bioconjug Chem. 2010 Jun 16;21(6):1043-55. doi: 10.1021/bc900542f.

Abstract

The development of a fluoride cleavable linker 1 for reversibly labeling (oligo)nucleotides is described here. The linker allows different ways of chemical attachment of a reporter molecule, for example, click chemistry or amide formation. The versatile attachment modes of labels are demonstrated by derivatizations with pyrene and fluorescein. Besides the synthesis of the new linker, we also show the derivatization of iodobenzene as a model compound and a nucleoside to demonstrate the applicability. Further, cleavability studies in solution and on a solid-supported oligonucleotide are shown. The linker can be applied in the synthesis of reversible terminators, useful for new DNA sequencing technologies like cyclic reversibly terminating (CRT) sequencing.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Fluorescein / chemistry
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorides / chemistry*
  • Oligonucleotides / chemistry*
  • Pyrenes / chemistry
  • Sequence Analysis, DNA / methods*
  • Staining and Labeling*

Substances

  • Fluorescent Dyes
  • Oligonucleotides
  • Pyrenes
  • pyrene
  • Fluorides
  • Fluorescein