RESOLUTION OF RACEMIC CARBOVIR AND SELECTIVE-INHIBITION OF HUMAN-IMMUNODEFICIENCY-VIRUS BY THE (-) ENANTIOMER

(+/-) Carbocyclic 2′,3′-didehydro-2′,3′-dideoxyguanosine (Carbovir; NSC 614846) is an antiretroviral agent which is undergoing preclinical evaluation for the treatment of AIDS. Racemic carbovir was separated into its D and L enantiomers by the action of adenosine deaminase on the 2,6-diaminopurine precursor. Subsequent evaluation of the enantiomers against human immunodeficiency virus type 1 revealed that the antiviral activity of carbovir resides in the (-) isomer that is analagous to the nucleoside, β-D-2′,3′-didehydro-2′,3′-dideoxyguanosine. © 1990.