Journal of Medicinal Chemistry p. 1507 - 1510 (1982)
Update date:2022-08-10
Topics:
Harrison, David H.
Schinazi, Raymond F.
Rubin, Byron H.
1-β-D-Arabinofuranosylthymine (aThy; ara-T) is a potent selective anti herpes simplex virus drug.Its anhydro analogue, 2,2'-anhydro-aThy, was shown to be 9-fold less active and at least 3-fold less toxic than aThy.This compound was relatively stable at physiological pH and in strong acid but was rapidly hydrolyzed in base with a half-life of 18.3 min.The three-dimensional crystal structure of 2,2'-anhydro-aThy revealed a rigid structure with the arabinose ring in the unusual O1' endo, pucker, conformation.The trans-gauche conformation.The trans-gauche conformation along the C4'-C5' bond permits only intermolecular hydrogen bonding of the 5'-hydroxy and O3'.
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