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卷 25, 期 43, 页码 7868-7872出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c03094
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A cyclic nucleoside has been designed and synthesized to introduce specific conformations into functional nucleic acids by fixing the rotation, base orientation, and sugar structure.
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 H-1 NMR and computational studies revealed that the sugar conformation, base orientation, and gamma 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.
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