ArticleJournal of the American Chemical Society2012
Evolutionary divergence of sedoheptulose 7-phosphate cyclases leads to several distinct cyclic products.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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23 citing papers in PubMed, 41 citations in OpenAlex.
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- Synthesis of the Carba-Analogs of the α-Pyranose and β-Pyranose Forms of Sedoheptulose 7-Phosphate and Probing the Stereospecificity of Sedoheptulose 7-Phosphate Cyclases.Biochemistry · 2024Article
- Unraveling the Molecular Basis of Mycosporine Biosynthesis in Fungi.International journal of molecular sciences · 2023Article
- Acarbose May Function as a Competitive Exclusion Agent for the Producing Bacteria.ACS chemical biology · 2023Article
- Biochemical Characterization of GacI, a Bifunctional Glycosyltransferase-Phosphatase Enzyme Involved in Acarbose Biosynthesis inBiochemistry · 2022Article
- Synthetic Optimizations for Gram-Scale Preparation of 1-Molecules (Basel, Switzerland) · 2022Article
- Complete biosynthetic pathway to the antidiabetic drug acarbose.Nature communications · 2022Article
- EDB Gene Cluster-Dependent Indole Production Is Responsible for the Ability ofJournal of natural products · 2022Article
- Leaf nodule endosymbiotic Burkholderia confer targeted allelopathy to their Psychotria hosts.Scientific reports · 2021Article
- Biosynthesis and Heterologous Production of Mycosporine-Like Amino Acid Palythines.The Journal of organic chemistry · 2021Article
- Parallel lives of symbionts and hosts: chemical mutualism in marine animals.Natural product reports · 2018Review
- Biosynthesis and Metabolic Engineering of Pseudo-oligosaccharides.Emerging topics in life sciences · 2018Article
- Mycosporine-Like Amino Acids for Skin Photoprotection.Current medicinal chemistry · 2018Review
- The sedoheptulose 7-phosphate cyclases and their emerging roles in biology and ecology.Natural product reports · 2017Review
- Evolution and Distribution of CACS chemical biology · 2017Article
- The plastid genome of some eustigmatophyte algae harbours a bacteria-derived six-gene cluster for biosynthesis of a novel secondary metabolite.Open biology · 2016Article
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- Structure of a sedoheptulose 7-phosphate cyclase: ValA from Streptomyces hygroscopicus.Biochemistry · 2014Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Sedoheptulose 7-phosphate cyclases are enzymes that utilize the pentose phosphate pathway intermediate, sedoheptulose 7-phosphate, to generate cyclic precursors of many bioactive natural products, such as the antidiabetic drug acarbose, the crop protectant validamycin, and the natural sunscreens mycosporine-like amino acids. These proteins are phylogenetically related to the dehydroquinate (DHQ) synthases from the shikimate pathway and are part of the more recently recognized superfamily of sugar phosphate cyclases, which includes DHQ synthases, aminoDHQ synthases, and 2-deoxy-scyllo-inosose synthases. Through genome mining and biochemical studies, we identified yet another subset of DHQS-like proteins in the actinomycete Actinosynnema mirum and the myxobacterium Stigmatella aurantiaca DW4/3-1. These enzymes catalyze the conversion of sedoheptulose 7-phosphate to 2-epi-valiolone, which is predicted to be an alternative precursor for aminocyclitol biosynthesis. Comparative bioinformatics and biochemical analyses of these proteins with 2-epi-5-epi-valiolone synthases (EEVS) and desmethyl-4-deoxygadusol synthases (DDGS) provided further insights into their genetic diversity, conserved amino acid sequences, and plausible catalytic mechanisms. The results further highlight the uniquely diverse DHQS-like sugar phosphate cyclases, which may provide new tools for chemoenzymatic, stereospecific synthesis of various cyclic molecules.
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