Synthetic Method for Oligonucleotide Block by Using Alkyl-Chain-Soluble Support

Org Lett. 2016 Feb 19;18(4):800-3. doi: 10.1021/acs.orglett.6b00077. Epub 2016 Feb 4.

Abstract

A straightforward method for the synthesis of oligonucleotide blocks using a Cbz-type alkyl-chain-soluble support (Z-ACSS) attached to the 3'-OH group of 3'-terminal nucleosides was developed. The Z-ACSS allowed for the preparation of fully protected deoxyribo- and ribo-oligonucleotides without chromatographic purification and released dimer- to tetramer-size oligonucleotide blocks via hydrogenation using a Pd/C catalyst without significant loss or migration of protective groups such as 5'-end 4,4'-dimethoxtrityl, 2-cyanoethyl on internucleotide bonds, or 2'-TBS.

MeSH terms

  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Nucleosides / chemistry
  • Oligonucleotides / chemical synthesis*
  • Oligonucleotides / chemistry

Substances

  • Nucleosides
  • Oligonucleotides