ArticleNature chemistry2012
Biosynthesis of the tunicamycin antibiotics proceeds via unique exo-glycal intermediates.
Article in Nature chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers, 1 of them a synthesis that pooled it.
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Who cites it
36 citing papers in PubMed, 1 synthesis or guideline pooled it.
- Links between the unfolded protein response and the DNA damage response in hypoxia: a systematic review.Biochemical Society transactions · 2021Pooled it
- Biosynthesis and Genome Mining Potentials of Nucleoside Natural Products.Chembiochem : a European journal of chemical biology · 2023Article
- Enzymatische C4-Epimerisierung von UDP-Glucuronsäure: präzise gesteuerte Rotation eines transienten 4-Ketointermediats für eine invertierende Reaktion ohne Decarboxylierung.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2023Article
- Enzymatic C4-Epimerization of UDP-Glucuronic Acid: Precisely Steered Rotation of a Transient 4-Keto Intermediate for an Inverted Reaction without Decarboxylation.Angewandte Chemie (International ed. in English) · 2023Article
- Draft genome sequence of3 Biotech · 2023Article
- Efficient biosynthesis of nucleoside cytokinin angustmycin A containing an unusual sugar system.Nature communications · 2021Article
- Biosynthesis of the nucleoside antibiotic angustmycins: identification and characterization of the biosynthetic gene cluster reveal unprecedented dehydratase required for exo-glycal formation.The Journal of antibiotics · 2021Article
- The regulation of ferroptosis by MESH1 through the activation of the integrative stress response.Cell death & disease · 2021Article
- Identification and characterization of enzymes involved in the biosynthesis of pyrimidine nucleoside antibiotics.Natural product reports · 2021Review
- PelX is a UDP-The Journal of biological chemistry · 2020Article
- Homologous expression of lysA encoding diaminopimelic acid (DAP) decarboxylase reveals increased antibiotic production in Streptomyces clavuligerus.Brazilian journal of microbiology : [publication of the Brazilian Society for Microbiology] · 2020Article
- Engineering of Streptomyces lividans for heterologous expression of secondary metabolite gene clusters.Microbial cell factories · 2020Article
- Don't sugarcoat it: How glycocalyx composition influences cancer progression.The Journal of cell biology · 2020Review
- Tunicamycin: chemical synthesis and biosynthesis.The Journal of antibiotics · 2019Review
- Mechanism of action of nucleoside antibacterial natural product antibiotics.The Journal of antibiotics · 2019Review
- Recent advances in the biosynthesis of nucleoside antibiotics.The Journal of antibiotics · 2019Review
- A Parsimonious Mechanism of Sugar Dehydration by Human GDP-Mannose-4,6-dehydratase.ACS catalysis · 2019Article
- Elucidation of the Herbicidin Tailoring Pathway Offers Insights into Its Structural Diversity.Organic letters · 2019Article
- Structures of DPAGT1 Explain Glycosylation Disease Mechanisms and Advance TB Antibiotic Design.Cell · 2018Article
- Analysis of the Tunicamycin Biosynthetic Gene Cluster of Streptomyces chartreusis Reveals New Insights into Tunicamycin Production and Immunity.Antimicrobial agents and chemotherapy · 2018Article
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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.
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