4'-Fluorinated carbocyclic nucleosides: synthesis and inhibitory activity against S-adenosyl-L-homocysteine hydrolase.

4'-Fluorinated analogue of 9-[(1'R,2'S,3'R)-2',3'-dihydroxy-cyclopentan-1'-yl]adenine (DHCaA) and their related analogues were systematically synthesized under the Mitsunobu and palladium(0) coupling conditions followed by fluorination with inversion of the configuration by using diethylaminosulfur trifluoride, respectively. 4'-beta-Fluoro DHCaA and 2-amino-4'-alpha-fluoro DHCaA demonstrated slight inhibitory activity against human and Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase, respectively.