Design and synthesis of new acid cleavable linkers for DNA sequencing by synthesis

Nucleosides Nucleotides Nucleic Acids. 2014;33(12):774-85. doi: 10.1080/15257770.2014.945647.

Abstract

A new kind of acid sensitive tetrahydrofuranyl (THF) linker was synthesized and then reacted with 5-(6)-carboxytetramethylrhodaminesuccinimidyl ester (5(6)-TAMRA, SE), followed by di(N-succinimidyl) carbonate (DSC) and modified 2'-deoxyuridine triphosphate (dUTP); the final product, as a reversible terminator for DNA sequencing by synthesis (DNA SBS), was given obtained and confirmed by 1H-NMR, 31P-NMR, and HRMS with purity of up to 99%. The synthesized dye-labeled terminator incorporated into DNA strand successfully, and the fluorophore was cleaved completely under acidic conditions. The preliminary results encourage us to explore more acid-sensitive linkers for DNA SBS to increase the cleavage efficiency under weakly acidic conditions.

Keywords: Triphosphate analogues; fluorescent base analogues; synthetic methodology.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Deoxyuracil Nucleotides / chemical synthesis*
  • Deoxyuracil Nucleotides / chemistry
  • Fluorescent Dyes / chemistry
  • Furans / chemical synthesis
  • Rhodamines / chemical synthesis*
  • Rhodamines / chemistry
  • Sequence Analysis, DNA / methods*

Substances

  • Deoxyuracil Nucleotides
  • Fluorescent Dyes
  • Furans
  • Rhodamines