(R)-2,4-Dihydroxybutyramide seco-pseudonucleosides: new versatile homochiral synthons for synthesis of modified oligonucleotides

Org Lett. 2002 Dec 26;4(26):4607-10. doi: 10.1021/ol0269289.

Abstract

[reaction: see text] Two series of seco-pseudonucleoside synthons were synthesized from (R)-(+)-alpha-hydroxy-gamma-butyrolactone and (R)-(-)-pantolactone by aminolysis, side-chain protection, dimethoxytritylation, and phosphitylation or solid-phase attachment. The phosphoramidites and solid supports were used in automated DNA synthesis to prepare oligonucleotides modified with one or more 2,4-dihydroxybutyramide units bearing side-chain reporter groups. These new oligonucleotide modification reagents allow the introduction of a label into any desired position within an oligonucleotide chain during solid-phase assembly.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Base Sequence
  • Combinatorial Chemistry Techniques / instrumentation
  • Drug Stability
  • Molecular Probes / chemical synthesis
  • Nucleic Acid Denaturation
  • Nucleosides / chemistry
  • Oligonucleotides / chemical synthesis*
  • Phosphites / chemistry
  • Stereoisomerism
  • Temperature

Substances

  • Amides
  • Molecular Probes
  • Nucleosides
  • Oligonucleotides
  • Phosphites
  • butyramide