title: Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase.
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.
authors.affiliation: Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, South Korea.
authors.forename: Hea Ok
authors.initials: HO
authors.lastname: Kim
authors.forename: Su Jeong
authors.initials: SJ
authors.lastname: Yoo
authors.forename: Hee Sung
authors.initials: HS
authors.lastname: Ahn
authors.forename: Won Jun
authors.initials: WJ
authors.lastname: Choi
authors.forename: Hyung Ryong
authors.initials: HR
authors.lastname: Moon
authors.forename: Kang Man
authors.initials: KM
authors.lastname: Lee
authors.forename: Moon Woo
authors.initials: MW
authors.lastname: Chun
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D043383:Adenosylhomocysteinase / Q000037:antagonists & inhibitors*; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D005461:Fluorine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy
chemical_list: D003517:Cyclopentanes; D004791:Enzyme Inhibitors; C494075:cyclopentenyladenine; D005461:Fluorine; D043383:Adenosylhomocysteinase; D000225:Adenine