Synthesis and biological activity of nucleoside antibiotics, ascamycin and its amino acid analogs.
Synthesis of an alanylsulfamoyl nucleoside antibiotic, ascamycin was achieved by the condensation of N6-t-butyloxycarbonyl-2-chloro-9-(2',3'-O-isopropylidene-5'-O-sulfamoyl- beta-D- ribofuranosyl)adenine(3) with t-butyloxycarbonyl-L-alanylimidazole in the presence of NaH in DMF. Deprotection with 90% trifluoroacetic acid gave ascamycin in 61% overall yield. This procedure may be applicable for preparation of a number of amino acid analogs of ascamycin.
D000241:Adenosine / Q000138:chemical synthesis / Q000031:analogs & derivatives; D000596:Amino Acids / Q000138:chemical synthesis; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D013329:Structure-Activity Relationship
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; C042369:ascamycin; D000241:Adenosine