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

Hea Ok Kim, Su Jeong Yoo, Hee Sung Ahn, Won Jun Choi, Hyung Ryong Moon, Kang Man Lee, Moon Woo Chun, Lak Shin Jeong

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

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.

Original languageEnglish
Pages (from-to)2091-2093
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume14
Issue number9
DOIs
StatePublished - 3 May 2004

Keywords

  • Antiviral
  • Carbocyclic nucleosides
  • Electrophilic fluorination
  • S-Adenosylhomocysteine hydrolase

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