Biosynthesis of the tunicamycin antibiotics proceeds via unique exo-glycal intermediates View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2012-05-20

AUTHORS

Filip J. Wyszynski, Seung Seo Lee, Tomoaki Yabe, Hua Wang, Juan Pablo Gomez-Escribano, Mervyn J. Bibb, Soo Jae Lee, Gideon J. Davies, Benjamin G. Davis

ABSTRACT

The tunicamycins are archetypal nucleoside antibiotics targeting bacterial peptidoglycan biosynthesis and eukaryotic protein N-glycosylation. Understanding the biosynthesis of their unusual carbon framework may lead to variants with improved selectivity. Here, we demonstrate in vitro recapitulation of key sugar-manipulating enzymes from this pathway. TunA is found to exhibit unusual regioselectivity in the reduction of a key α,β-unsaturated ketone. The product of this reaction is shown to be the preferred substrate for TunF—an epimerase that converts the glucose derivative to a galactose. In Streptomyces strains in which another gene (tunB) is deleted, the biosynthesis is shown to stall at this exo-glycal product. These investigations confirm the combined TunA/F activity and delineate the ordering of events in the metabolic pathway. This is the first time these surprising exo-glycal intermediates have been seen in biology. They suggest that construction of the aminodialdose core of tunicamycin exploits their enol ether motif in a mode of C–C bond formation not previously observed in nature, to create an 11-carbon chain. More... »

PAGES

539-546

Identifiers

URI

http://scigraph.springernature.com/pub.10.1038/nchem.1351

DOI

http://dx.doi.org/10.1038/nchem.1351

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1023315504

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/22717438


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