Synthesis of fluorescent nucleoside analogs as probes for 2'-deoxyribonucleoside kinases.

We are reporting on the synthesis of fluorescent nucleoside analogs with modified sugar moieties (e.g., sugars other than ribose and 2'-deoxyribose). Four novel derivatives of the fluorescent thymidine analog 6-methyl-3-(beta-D-2'-deoxyribofuranosyl) furano-[2,3-d]pyrimidin-2-one were synthesized via Sonogashira reaction and subsequent copper-catalyzed cycloaddition. These compounds represent promising tools for studying nucleoside metabolism inside living cells, as well as for screening directed evolution libraries of 2'-deoxyribonucleoside kinases with new and improved activity for the corresponding nucleoside analogs. Copyright (c) 2009 Elsevier Ltd. All rights reserved.