Efficient chemical synthesis of N²-modified guanosine derivatives: a versatile probes for mRNA labeling

Abstract

An efficient method for the synthesis of N²-modified guanosine nucleotides such as N²-[benzyl-N-(propyl)carbamate]-guanosine-5′-O-monophosphate, N²-[benzyl-N-(propyl)carbamate]-guanosine-5′-O-diphosphate, N²-[benzyl-N-(propyl)carbamate]-guanosine-5′-O-triphosphate, and N²-[benzyl-N-(propyl)carbamate]-N⁷-methyl-guanosine-5′-O-diphosphate, starting from the corresponding nucleotide is described. The overall reaction involves the condensation between the exocyclic amine of guanosine nucleotide with 3-[(benzyloxycarbonyl)amino]propionaldehyde in aqueous methanol, followed by reduction using sodium cyanoborohydride to furnish the corresponding N²-modified guanosine nucleotide in moderate yield with high purity (>99.5%).

Keywords:

• Nucleic acid
• N2-alkylguanine
• oligonucleotides
• mRNA cap
• DNA

Additional information

Funding

The author(s) reported there is no funding associated with the work featured in this article.