Resolution of racemic carbovir and selective inhibition of human immunodeficiency virus by the (-) enantiomer

R Vince; J Brownell

doi:10.1016/0006-291x(90)91115-9

Resolution of racemic carbovir and selective inhibition of human immunodeficiency virus by the (-) enantiomer

Biochem Biophys Res Commun. 1990 May 16;168(3):912-6. doi: 10.1016/0006-291x(90)91115-9.

Authors

R Vince¹, J Brownell

Affiliation

¹ Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, Minneapolis 55455.

PMID: 2346492
DOI: 10.1016/0006-291x(90)91115-9

Abstract

(+-) 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.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Antiviral Agents / pharmacology*
Dideoxynucleosides / pharmacology*
HIV-1 / drug effects*
Microbial Sensitivity Tests
Stereoisomerism

Substances

Antiviral Agents
Dideoxynucleosides
carbovir

Grants and funding

CA23263/CA/NCI NIH HHS/United States