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 nucleoside dimers as substrates. Nucleoside trimer and tetramer were synthesized by derivatization reactions.

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Publication Details

Journal
Organic Letters
Published
2024-12-10
DOI
https://doi.org/10.1021/acs.orglett.4c04024
Citations
1
Primary Topic
HIV/AIDS drug development and treatment
Type
article
Field-Weighted Citation Impact
0.39

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article

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

Ao-Di Ma, Wen‐Wu Sun, Bin Wu, Weijia Chen
1 citations
Organic Letters
HIV/AIDS drug development and treatment
0.39
article

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

Ao-Di Ma, Wen‐Wu Sun, Bin Wu, Weijia Chen
article en
1 citations

Abstract

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.

Organic LettersVol. 26(50)
Minzu University of China (CN), State Ethnic Affairs Commission (CN)
National Natural Science Foundation of China, South-Central University for Nationalities, Fundamental Research Funds for the Central Universities
Clean water and sanitation
Openalex Percentile: Top 34%
HIV/AIDS drug development and treatment
0.39
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