Azasugars replace the ring oxygen found in cyclic monosaccharides with a nitrogen atom. Despite their widespread use as glycosidase inhibitors, details on their biosynthesis, structural diversity, distribution and chemical ecology have received scant attention. It is known that a three gene cluster(3GC) coding for aminotransferase, phosphatase and dehydrogenase enzymes represents the minimum biosynthetic unit for an azasugar. We employed the Enzyme Similarity Tool (EST) to identify 3GCs in hundreds of microbial species. From these data we derived a consensus sequence for the aminotransferase enzyme that is found in what is an otherwise unconserved region of the broader aminotransferase class these enzymes reside in. Most of the 3GCs we identified were in Bacillus and Streptomyces species isolated from soil rhizosphere environments, but some 3GCs were identified in more diverse species such as nematode symbionts Photorhabdus and Xenorhabdus, the human skin commensal Cutibacterium acnes, and the marine Streptomyces sp. ADLI95-17 and Bacillus sp. SPB7, both symbionts to sea sponges. We suggest that this study of the azasugar 3GC signature will facilitate identification of new azasugar producers.

Exploring the hallmark signature of microbial azasguar biosynthesis through comparative genomic analysis

ACS Spring Meeting 2021

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