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

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...

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Bibliographic Details
Published inOrganic letters Vol. 26; no. 50; pp. 10891 - 10896
Main Authors Ma, Ao-Di, Chen, Wei-Jia, Sun, Wen-Wu, Wu, Bin
Format Journal Article
LanguageEnglish
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
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Summary: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 nucleoside dimers as substrates. Nucleoside trimer and tetramer were synthesized by derivatization reactions.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c04024