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Abstract
2'-Deoxy-2'-fluoroguanylyl-(3'-5')-uridine (GfpU) was synthesized as a non-hydrolyzable substrate analog of ribonuclease T1. 2'-Deoxy-2'-fluoroguanosine was derivatized to the N2-isobutyryl-5'-monomethoxytrityl compound and condensed with 2', 3'-di-O-acetyluridine 5'-monophosphate by the use of dicyclohexylcarbodiimide to obtain GfpU. For structural elucidation of the dinucleoside monophosphate, 2'-deoxy-2'-fluoroguanosine 3'-monophosphate was also synthesized. The conformation of GfpU was found to take a right-handed, weakly stacked form as deduced by ultraviolet, circular dichroism, and nuclear magnetic resonance (NMR) spectroscopy.
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