Details for Patent: 6,069,252

Title:	Method of resolution and antiviral activity of 1,3-oxathiolane nucleoside enantiomers
Abstract:	A process for the resolution of a racemic mixture of nucleoside enantiomers that includes the step of exposing the racemic mixture to an enzyme that preferentially catalyzes a reaction in one of the enantiomers. The nucleoside enantiomer (-)-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is an effective antiviral agent against HIV, HBV, and other viruses replicating in a similar manner.
Inventor(s):	Liotta; Dennis C. (Stone Mountain, GA), Schinazi; Raymond F. (Decatur, GA), Choi; Woo-Baeg (North Brunswick, NJ)
Assignee:	Emory University (Atlanta, GA)
Filing Date:	Jun 07, 1995
Application Number:	08/474,406
Claims:	1. A (+)-.beta.-D-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane compound at least 95% free of the corresponding (-)-.beta.-enantiomer of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are selected from the group consisting of acetyl, propionyl, butyryl, and pentanoyl or R.sub.1 can be a mono, di or triphosphate ester, and one of R.sub.1 or R.sub.2 can be hydrogen, or a physiologically acceptable salt thereof. 2. The 5'-phosphate ester of the compound of claim 1. 3. The 5'-monophosphate ester of the compound of claim 1. 4. The 5'-diphosphate ester of the compound of claim 1. 5. The 5'-triphosphate ester of the compound of claim 1. 6. The compound of claim 1 wherein R.sub.1 is acetyl and R.sub.2 is hydrogen. 7. (+)-.beta.-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane, or a physiologically acceptable salt thereof, substantially in the absence of its corresponding (-)-.beta.-L-enantiomer. 8. A (+)-.beta.-D-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane compound substantially in the absence of its corresponding (-)-.beta.-L-enantiomer of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are selected from the group consisting of acetyl, propionyl, butyryl, and pentanoyl or R.sub.1 can be a mono, di or triphosphate ester, and one of R.sub.1 or R.sub.2 can be hydrogen, or a physiologically acceptable salt thereof. 9. (+)-.beta.-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane, or a physiologically acceptable salt thereof, at least 95% free of the corresponding (-)-.beta.-enantiomer.