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.
Original language | English |
---|---|
Pages (from-to) | 9891-9897 |
Number of pages | 7 |
Journal | Bioorganic and Medicinal Chemistry |
Volume | 16 |
Issue number | 23 |
DOIs | |
State | Published - 1 Dec 2008 |
Keywords
- 2′,3′-Dideoxy-4′-selenonucleosides
- 2′,3′-Dideoxycytidine
- Anti-HIV agents
- Pummerer type condensation
- South conformation