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ID: ALA1147541

Journal: Bioorg Med Chem Lett

Title: Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase.

Authors: Kim HO, Yoo SJ, Ahn HS, Choi WJ, Moon HR, Lee KM, Chun MW, Jeong LS.

Abstract: Fluoro-DHCeA (4) was efficiently synthesized from d-cyclopentenone derivative 5 using electrophilic fluorination as a key step. Fluoro-DHCeA (4) was found to be as potent as DHCeA (3), but exhibited irreversible inhibition of enzyme unlike DHCeA (3) showing reversible inhibition. From this study, 4(')-hydroxymethyl groups of neplanocin A and fluoro-neplanocin A played an important role in binding to the active site of the enzyme.

CiteXplore: 15080985

DOI: 10.1016/j.bmcl.2004.02.039