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Angew Chem Int Ed Engl. 2015 Oct 19;54(43):12550-2. doi: 10.1002/anie.201507120. Epub 2015 Sep 7.

Natural 1,3-Dipolar Cycloadditions.

Author information

1
Department of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology (HKI), Beutenbergstr. 11a, 07745 Jena (Germany).
2
Department of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology (HKI), Beutenbergstr. 11a, 07745 Jena (Germany). christian.hertweck@leibniz-hki.de.
3
Friedrich Schiller University, Jena (Germany). christian.hertweck@leibniz-hki.de.

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.

KEYWORDS:

[3+2] cycloaddition; decarboxylation; flavin coenzyme; prenyl transferase; ubiquinone biosynthesis

PMID:
26465651
DOI:
10.1002/anie.201507120
[Indexed for MEDLINE]

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