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Spicamycin

 

 

Spicamycin was isolated in 1983 from the culture broth of Streptomyces alanosinicus as a potent antitumor antibiotic.  Structural features of spicamycin include an aminoheptose, adenine, glycine, and various fatty acids. An unusual linkage of adenine C-6 amino group as the b-manno anomeric to an aminoheptose moiety as well as the attachment point of the adenine makes the spicamycin structure interesting.  Naturally occurring spicamycin exists as a mixture of several congers differing in their fatty acid moieties.

 

Because of its unusual structure, alternative mechanism of action, and non-overlapping toxicities, spicamycin is an interesting target for total synthesis.