Synthesis and application of a novel, crystalline phosphoramidite monomer with thiol terminus, suitable for the synthesis of DNA conjugates

Bioorg Med Chem. 2001 May;9(5):1241-7. doi: 10.1016/s0968-0896(00)00339-4.

Abstract

A new, crystalline 5'-thiol modifier phosphoramidite monomer (3), suitable for DNA synthesis, has been prepared. This monomer has been built into an oligonucleotide using the standard protocol. After cleavage, purification and removal of the trityl group with Ag(+), a free 5'-thiol terminal oligonucleotide (15) has been obtained which was subsequently coupled to a cysteine derivative via a disulfide bridge to afford conjugate 16.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromans / chemical synthesis*
  • Chromans / urine*
  • Chromatography, High Pressure Liquid
  • Cysteine / analogs & derivatives
  • Cysteine / chemistry*
  • Disulfides / chemistry*
  • Oligonucleotides / chemical synthesis*
  • Oligonucleotides / isolation & purification
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry*
  • Pentanoic Acids / chemical synthesis*
  • Pentanoic Acids / urine*
  • Spectrometry, Mass, Electrospray Ionization
  • Sulfhydryl Compounds / chemistry*

Substances

  • 5-(6-hydroxy-2,5,7,8-tetramethyl-chroman-2-yl)-2-methyl-pentanoic acid
  • Chromans
  • Disulfides
  • Oligonucleotides
  • Organophosphorus Compounds
  • Pentanoic Acids
  • Sulfhydryl Compounds
  • phosphoramidite
  • Cysteine