Synthesis and Characterization of the Dinucleoside Monophosphates Containing 2/-HaIogeno-2′-deoxyadenosines
摘要：
To elucidate the correlation between the structure and biological activity of 2/-substituted, 2/-deoxypurinenucIeoside derivatives, six ApA anologs containing 2/-fluoro-2/-deoxyadenosine (dAfl) and 2/-chloro-2/~deoxyadenosine (dAcl) were synthesized and characterized by UV ab sorption, CD and H-NMR spectroscopy. The dAfl derivatives have much higher population of CW-endo puckering than adenosine in a furanose conformational equilibrium. The dAcl derivatives have similar C3′-endo population to that of adenosine. The experimental results suggest that the dAfl-containing dimers take a stacked conformation similar to that of ApA but with larger degree of stacking. The extent of stacking decreases in the following order: dAflpdAfl>dAflpA=ApdAfl>ApA. The dAcl-containing dimers take a stacked conformation similar both in the mode an! degree to that of ApA. These results show that C3f-en do puckering in both residues is required for optimum stacking in a ribo-dimer. The effects of 2/-substituents on polynucleotide conformation are discussed.
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DOI：
10.1246/nikkashi.1981.851
被引量：
年份：
1981
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