An efficient synthesis of 3′-O-triazole modified guanosine-5′-O-monophosphate using click chemistry

Abstract

First chemical synthesis of 3′-O-1,2,3-triazolyl-guanosine-5′-O-monophosphate by copper catalyzed click chemistry is described. The present cycloaddition reaction involves, in situ generation of azide from the corresponding bromide followed by copper catalyst cycloaddition with 3′-O-propargyl guanosine monophosphate in water, in the presence of catalytic amount of β-cyclodextrin. The CuAAC reaction is highly regioselective forming 1,4-cycloadduct with good yield and high purity. The final compound, 3′-O -triazole substituted guanosine monophosphate has the potential to use in various biomolecules such as labeled nucleic acids, mRNA dinucleotide cap analogs for molecular biology and their applications in the therapeutic field.

Keywords:

• 3′-O -triazole substituted guanosine monophosphate
• Copper catalyst
• β-Cyclodextrin
• Click Chemistry