title: Natural 1,3-Dipolar Cycloadditions.
abstract: [3+2] in the wild: Biomimetic natural product syntheses and theoretical considerations have indicated that 1,3-dipolar cycloadditions take place in nature. Now, the structure, biosynthesis, and function of a heavily modified prenylated flavin cofactor have been elucidated. In the azomethine ylide form, it undergoes [3+2] cycloadditions with aromatic acids and promotes their decarboxylation.
authors.affiliation: Department of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology (HKI), Beutenbergstr. 11a, 07745 Jena (Germany).
authors.forename: Martin
authors.initials: M
authors.lastname: Baunach
authors.affiliation: Department of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology (HKI), Beutenbergstr. 11a, 07745 Jena (Germany). christian.hertweck@leibniz-hki.de.|Friedrich Schiller University, Jena (Germany). christian.hertweck@leibniz-hki.de.
authors.forename: Christian
authors.initials: C
authors.lastname: Hertweck
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D032701:Biomimetics / Q000379:methods; D002262:Carboxy-Lyases / Q000378:metabolism; D003500:Cyclization; D061565:Cycloaddition Reaction / Q000379:methods*; D003653:Decarboxylation; D004926:Escherichia coli / Q000201:enzymology; D029968:Escherichia coli Proteins / Q000378:metabolism; D005415:Flavins / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D008958:Models, Molecular; D012441:Saccharomyces cerevisiae / Q000201:enzymology; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D029968:Escherichia coli Proteins; D005415:Flavins; D013882:Thiosemicarbazones; C512188:azomethine; D002262:Carboxy-Lyases; C087194:phenylacrylic acid decarboxylase; C113304:ubiX protein, E coli
keywords: [3+2] cycloaddition; decarboxylation; flavin coenzyme; prenyl transferase; ubiquinone biosynthesis