Synthesis and biological activity of nucleoside antibiotics, ascamycin and its amino acid analogs
Ubukata, M.; Osada, H.; Isono, K.
Nucleic Acids Symposium Series 16: 81-83
1985
ISSN/ISBN: 0261-3166 PMID: 3841391 Document Number: 245973
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.
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