Stereoselective synthesis of nucleoside analogues
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United States of America Patent
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Apr 1, 2003
Grant Date -
Jan 17, 2002
app pub date -
Feb 9, 2001
filing date -
Feb 11, 2000
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Abstract
The invention is a process for stereoselectively producing a dioxolane nucleoside analogue from an anomeric mixture of .beta. and .alpha. anomers represented by the following formula A or formula B: ##STR1## wherein R is selected from the group consisting of C.sub.1-6 alkyl and C.sub.6-15 aryl and Bz is benzoyl. The process comprises hydrolyzing said mixture with an enzyme selected from the group consisting of Protease N, Alcalase, Savinase, ChiroCLEC-BL, PS-30, and ChiroCLEC-PC to stereoselectively hydrolyze predominantly one anomer to form a product wherein R.sub.1 is replaced with H. The process also includes the step of separating the product from unhydrolyzed starting material. Additionally, the functional group at the C4 position is stereoselectively replaced with a purinyl or pyrimidinyl or derivative thereof.
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