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Ascamycin (ACM) and dealanylascamycin (DACM) are nucleoside antibiotics elaborated by  Streptomyces sp . JCM9888. The later shows broad spectrum inhibition activity to various gram-positive and gram-negative bacteria, eukaryotic  Trypanosoma  and is also toxic to mice, while ascamycin is active against very limited microorganisms, such as  Xanthomonas . Both compounds share an unusual 5′- O -sulfonamide moiety which is attached to an adenosine nucleoside. In this paper, we first report on the 30 kb gene cluster (23 genes,  acmA  to  acmW ) involved in the biosynthesis of these two antibiotics and a biosynthetic assembly line was proposed. Of them, six genes (AcmABGKIW) are hypothetical genes involved in 5′-O-sulfonamide formation. Two flavin adenine dinucleotide (FAD)-dependent chlorinase genes  acmX  and  acmY  were characterized which are significantly remote from  acmA-W  and postulated to be required for adenine C2-halogenation. Notably gene disruption of  acmE  resulted in a mutant which could only produce dealanylascamycin but was blocked in its ability to biosynthesize ascamycin, revealing its key role of conversion of dealanylascamycin to ascamycin.

Characterization of Biosynthetic Genes of Ascamycin/Dealanylascamycin Featuring a 5′-O-Sulfonamide Moiety in Streptomyces sp. JCM9888