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 analogous to the nucleoside, beta-D-2',3'-didehydro-2',3'-dideoxyguanosine.
Vince
R
R
Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, Minneapolis 55455.
Brownell
J
J
D000998:Antiviral Agents / Q000494:pharmacology*; D015224:Dideoxynucleosides / Q000494:pharmacology*; D015497:HIV-1 / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D013237:Stereoisomerism
D000998:Antiviral Agents; D015224:Dideoxynucleosides; C057503:carbovir