Access to 1'-Amino Carbocyclic Phosphoramidite to Enable Postsynthetic Functionalization of Oligonucleotides

Org Lett. 2021 Sep 3;23(17):6735-6739. doi: 10.1021/acs.orglett.1c02302. Epub 2021 Aug 23.

Abstract

We report a synthesis of a carbocyclic, abasic RNA phosphoramidite decorated with an amino functionality. The building block was efficiently incorporated into an RNA oligonucleotide in a site-specific manner, followed by deprotection to a free amino group. The amino moiety could be further derivatized as exemplified with fluorescein N-hydroxysuccinimide ester. Hence, this convertible building block may provide access to a variety of RNA oligonucleotides via postsynthetic amino group functionalization. In particular, providing a vector toward nucleobase replacements.

MeSH terms

  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oligonucleotides / chemical synthesis*
  • Oligonucleotides / chemistry
  • Organophosphorus Compounds / chemistry*
  • RNA / chemical synthesis*
  • RNA / chemistry

Substances

  • Oligonucleotides
  • Organophosphorus Compounds
  • phosphoramidite
  • RNA