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Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents
- Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents
- Jeong L.S.; Choi Y.N.; Tosh D.K.; Choi W.J.; Kim H.O.; Choi J.
- Ewha Authors
- 정낙신; 최원준
- Issue Date
- Journal Title
- Bioorganic and Medicinal Chemistry
- vol. 16, no. 23, pp. 9891 - 9897
- SCI; SCIE; SCOPUS
- On the basis of potent anti-HIV activity of 2',3'-dideoxynucleosides (ddNs), their bioisosteric analogues, 2',3'-dideoxy-4'-selenonucleosides (4'-seleno-ddNs) were first synthesized from a chiral template, d-glutamic acid using stereoselective ring-closure reaction of the dimesylate with Se2- and Pummerer type condensation of the selenoxide with nucleobases as key steps. X-ray crystallographic analysis indicated that 4'-seleno-ddNs adopted the same C2'-endo/C3'-exo (South) conformation as anti-HIV active ddNs, but did not show anti-HIV activity, indicating that RT seems to prefer the C2'-exo/C3'-endo (North) conformation on binding with their triphosphates. © 2008 Elsevier Ltd. All rights reserved.
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