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Nucleic Acids Symposium Series 2003 3(1):19-20; doi:10.1093/nass/3.1.19
© 2003 by Oxford University Press
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Synthesis of 3'-fluoro analogue of Cl-IB-MECA as adenosine A3 receptor ligand

Moon Woo Chun1, Moo Hong Lim1, Hyung Ryong Moon2, Hea Ok Kim2, Kenneth A. Jacobson3 and Lak Shin Jeong2

1 College of Pharmacy, Seoul National University, Seoul 151-742, Korea, 2 Laboratory of Medicinal Chemistry, Collage of Pharmacy, Ewha Womans University, Seoul 120-750, Korea, 3 Molecular Recognition Section, Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Disease, NIH, Bethesda, Maryland 20892, USA

3'-Fluoro analogue 1 of selective and potent adenosine A3 receptor agonist, Cl-IB-MECA was synthesized from D-xylose via highly regioselective opening of lyxo-epoxide 4 with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A3 adenosine receptor, the corresponding 3'-fluoro derivative showed remarkably decreased binding aftinity, indicating that 3'-hydroxyl group acts as hydrogen bonding donor, not hydrogen bonding acceptor like fluorine atom in binding to the A3 adenosine receptor.


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