Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S -adenosylhomocysteine hydrolase

Bioorganic & Medicinal Chemistry Letters
2004.0

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.

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