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Design, Synthesis, and Characterization of Photolabeling Probes for the Study of the Mechanisms of the Antiviral Effects of Ribavirin
Author(s) -
Wu Qiongyou,
Qu Fanqi,
Wan Jinqiao,
Zhu Xun,
Xia Yi,
Peng Ling
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490079
Subject(s) - ribavirin , chemistry , context (archaeology) , nucleoside , combinatorial chemistry , nucleoside analogue , stereochemistry , biochemistry , paleontology , biology , genotype , gene
Ribavirin, the only small molecule available so far for treating hepatitis‐C‐virus infection, was recently used in an emergency context to treat patients with severe acute respiratory syndrome (SARS) in the early stages of the disease. To study the mechanisms responsible for the antiviral effects of ribavirin by using a photolabeling approach, we designed, synthesized, and characterized the azidotriazole nucleosides 1 and 2 as photolabeling probes of ribavirin. These probes were synthesized either by performing nucleophilic substitution of the corresponding bromotriazole nucleoside with NaN 3 ( Scheme 2 ) or by directly coupling the azidotriazole with the protected ribose sugar ( Scheme 4 ). The azidotriazole nucleosides 1 and 2 showed a fast, clear‐cut photochemical reaction, which suggests that they are promising candidates for use in photolabeling studies.