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Title:   Author  item
                                            Price, Neilitem
                                            Bowman, Michaelitem
                                            CHEN, WENQING - Wuhan Universityitem
                                            DENG, ZIXIN - Shanghai Jiaotong University
  Submitted to: Meeting Abstract
                                    Publication Type: Abstract Only
                                    Publication Acceptance Date: 3/25/2011
                                    Publication  Date: 3/25/2011
                                    Citation: Price, N.P., Bowman, M.J., Chen, W., Deng, Z. 2011. Biosynthesis of the tunicamycins: Translocase-I inhibitors that target the synthesis of bacterial peptidoglycan and eukaryotic N-glycoproteins [abstract]. University of Waterloo, Ontario, Canada, Department of Biology Seminar Series. p. 2.Interpretive Summary:
                                Technical Abstract: The tunicamycins are a group of natural products that target the biosynthesis of bacterial peptidoglycan and eukaryotic N-glycoproteins.  The mechanism of action is known, with the tunicamycins established as transition state analogs for hexosamine-1-phosphate:prenol phosphate translocases.  Hence, this inhibits the formation of N-acetylmuramyl-undecanol pyrophosphate in bacteria or N-acetylglucosamine-dolichol pyrophosphate in eukaryotes, which are essential intermediates in these organisms.  We have investigated the biosynthesis of the tunicamycins by certain streptomyces species, and have proposed a pathway in which the 11-carbon dialdose sugar, tunicamine, is derived from uridine and N-acetylglucosamine.  Once formed the uridyl-tunicaminyl intermediate is a,ß-1,11-glycosylated and N-acylated to form the bioactive compounds prior to secretion.  Using heterologous expression we have identified twelve tun genes (tunA – tunL) responsible for tunicamycin biosynthesis in the producing organisms Streptomyces chartreusis and S. clavuligerus.  Amongst these is a putative radical SAM enzyme (TunB) with a potentially unique role in biosynthetic carbon-carbon bond formation, and an unusual glycosyltransferase involved in the formation of the anomeric-to-anomeric a,ß-1,11-glycosidic bond.  Hence, a seven-step novel pathway is proposed for tunicamycin biosynthesis which may be useful for the design of new tunicamycin analogs with selective/enhanced translocase specificity.


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