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Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents

Title
Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents
Authors
Jeong L.S.Choi Y.N.Tosh D.K.Choi W.J.Kim H.O.Choi J.
Ewha Authors
정낙신최원준
Issue Date
2008
Journal Title
Bioorganic and Medicinal Chemistry
ISSN
0968-0896JCR Link
Citation
vol. 16, no. 23, pp. 9891 - 9897
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
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.
DOI
10.1016/j.bmc.2008.10.034
Appears in Collections:
약학대학 > 약학과 > Journal papers
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