Amino acid analogs of benanomicin A through desalaninebenanomicin A.
Desalaninebenanomicin A has been synthesized in good yield by the cleavage of the amido bond of benanomicin A using MEERWEIN's reagent. This is a useful intermediate to prepare amino acid analogs of benanomicin A. MEERWEIN's reagent reacts with totally protected benanomicin A to give a stable imino ether. After deprotection, the imino ether is treated with aqueous acetone at reflux to afford a methyl ester of desalaninebenanomicin A. Desalaninebenanomicin A was coupled with a variety of amino acids by the active ester method to afford new benanomicin analogs.
Ikeda
D
D
Institute of Microbial Chemistry, Tokyo, Japan.
Nishizuka
T
T
Huang
S P
SP
Kondo
S
S
Takeuchi
T
T
D000596:Amino Acids / Q000737:chemistry*; D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry; D005658:Fungi / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D009279:Naphthacenes / Q000138:chemical synthesis* / Q000494:pharmacology; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013329:Structure-Activity Relationship; D000095643:Pradimicins and Benanomicins
D000596:Amino Acids; D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D000935:Antifungal Agents; D009279:Naphthacenes; C056805:benanomicin A; D000095643:Pradimicins and Benanomicins; C078938:desalaninebenanomicin A