Late-Stage Functionalization of Guanine-Based Nucleosides, Nucleotides, and Oligonucleotide: Synthesis and Derivatization of Tricyclic Nucleoside Analogues

• Published in: Organic letters Vol. 26; no. 50; pp. 10891 - 10896
• Main Authors: Ma, Ao-Di, Chen, Wei-Jia, Sun, Wen-Wu, Wu, Bin
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 20.12.2024
• Subjects: Antiviral Agents - chemical synthesis; Antiviral Agents - chemistry; Antiviral Agents - pharmacology; Catalysis; Cyclization; Guanine - chemistry; Molecular Structure; Nucleosides - chemical synthesis; Nucleosides - chemistry; Nucleotides - chemical synthesis; Nucleotides - chemistry; Oligonucleotides - chemical synthesis; Oligonucleotides - chemistry; Propane - analogs & derivatives; Propane - chemical synthesis; Propane - chemistry

We report here the synthesis of tricyclic nucleoside analogues via acid-catalyzed cyclization of guanine with 1,1,3,3-tetramethoxypropane. The method enables the use of hydroxyl-unprotected antiviral drugs (acyclovir, ganciclovir, and penciclovir), guanosines, oligonucleotide, and triazole-linked nu...