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 language | English |
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Pages (from-to) | 2091-2093 |
Number of pages | 3 |
Journal | Bioorganic and Medicinal Chemistry Letters |
Volume | 14 |
Issue number | 9 |
DOIs | |
State | Published - 3 May 2004 |
Keywords
- Antiviral
- Carbocyclic nucleosides
- Electrophilic fluorination
- S-Adenosylhomocysteine hydrolase