Design and Facile Synthesis of New Dinucleotide Cap Analog Containing Both 2' and 3'-OH Modification on M⁷Guanosine Moiety

Nucleosides Nucleotides Nucleic Acids. 2015;34(9):611-9. doi: 10.1080/15257770.2015.1041643.

Abstract

The first example of the synthesis of new dinucleotide cap analog containing 2('),3(')-diacetyl group on m(7)guanosine moiety is described. The desired modified cap analog, m(7,2)(')(,3)(')(-diacetyl)G[5(')]ppp[5(')]G has been obtained by the coupling reaction of triethylamine salt of m(7,2)(')(,3)(')(-diacetyl)GDP with ImGMP in presence of ZnCl2 as a catalyst in 62% yield with high purity. The structure of new cap analog has been confirmed by (1)H and (31)P NMR and mass data.

Keywords: 5′-capped mRNA; Cap analog; dendritic cells; diacetyl cap analog.

MeSH terms

  • Guanosine / analogs & derivatives*
  • Guanosine / chemical synthesis
  • Guanosine / chemistry*
  • RNA Cap Analogs / chemical synthesis
  • RNA Cap Analogs / chemistry*
  • RNA, Messenger / chemistry

Substances

  • RNA Cap Analogs
  • RNA, Messenger
  • Guanosine