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Synthesis and Conformational Analyses of Cyclonucleoside Having 13-Membered Ring Bridging Nucleobase and 5'-Position via a Linker Containing Sulfonamide.
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- Additional Information
- Source:
Publisher: American Chemical Society Country of Publication: United States NLM ID: 100890393 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1523-7052 (Electronic) Linking ISSN: 15237052 NLM ISO Abbreviation: Org Lett Subsets: MEDLINE
- Publication Information:
Original Publication: Washington, DC : American Chemical Society, c1999-
- Subject Terms:
- Abstract:
A cyclic nucleoside has been designed and synthesized to serve as a conformationally fixed building block for the development of functional oligonucleotides. The bridge was introduced between the nucleobase and the 5'-position to fix the rotation around the C4'-C5' bond, the base orientation, and the sugar puckering all at once. The 13-membered cyclic structure was introduced using a sulfonamide linkage, which retains an N-H group that can be used to attach an additional nucleoside moiety. The sulfonamide linkage was formed through the end-to-end cyclization of an intermediate that contained both a sulfonyltriazole and amino groups. Both 1 H NMR and computational studies revealed that the sugar conformation, base orientation, and γ torsion angle were S -type, anti , and trans , respectively. As such, cyclic nucleosides show promise for introducing these specific distorted conformations into functional nucleic acids.
- Accession Number:
0 (Nucleosides)
0 (Oligonucleotides)
0 (Nucleic Acids)
0 (Sugars)
- Publication Date:
Date Created: 20231019 Date Completed: 20231106 Latest Revision: 20231206
- Publication Date:
20231215
- Accession Number:
10.1021/acs.orglett.3c03094
- Accession Number:
37857270
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