Actinamine structure

Eor shaping the 1,3-diaminocyclitol into its final configuration and into the actinamine structure, first an epimerization step has to invert the stereochemical placement of the 2-hydroxyl group, which is proposed to be catalyzed by the SpcD enzyme, being related to sugar epimerases second, the actinamine branch... 

Spectinomycin (see Scheme 19) has a tricyclic structure, and contains actinamine. In aqueous solution, the carbonyl group is present in hydrated form. 

The spectinomycins (O Fig. 20) have a fused three-ring system which consists of a 4,5-disub-stituted actinamine and an ulose. Spectinomycin is produced by Streptomyces spectabilis and Streptomyces flavopersius. It has been clinically used for treatment of the gonorrhea infection. A related structure has been discovered with spenolimycin which was isolated from the culture filtrate of Streptomyces gilvospiralis. Efforts have been directed toward semisynthetic aminoglycoside antibiotics to treat multi-drug resistant bacteria [94]. 

The remaining six carbon atoms of the actinospectacin molecule are accounted for by the sugar moiety, which has been named actinospectose. Two reports have appeared concerning the structure of this sugar and the manner in which it is linked with actinamine. Tarbell and coworkers " examined the products obtained by treating actinospectacin with alkali... 

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