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Molecules 2016, 21(11), 1443; doi:10.3390/molecules21111443

Characterisation of the Broadly-Specific O-Methyl-transferase JerF from the Late Stages of Jerangolid Biosynthesis

1
Zentrum für Biomolekulare Wirkstoffe, Leibniz-Universität Hannover, Schneiderberg 38, 30167 Hannover, Germany
2
Professur für Organische Chemie (Lebensmittelchemie), Fakultät für Biologie, Chemie und Geowissenschaften, Universitätsstraße 30, 95447 Bayreuth, Germany
*
Author to whom correspondence should be addressed.
Academic Editor: Tobias A. M. Gulder
Received: 4 October 2016 / Revised: 20 October 2016 / Accepted: 21 October 2016 / Published: 29 October 2016
(This article belongs to the Special Issue Biosynthesis of Natural Products)
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Abstract

We describe the characterisation of the O-methyltransferase JerF from the late stages of jerangolid biosynthesis. JerF is the first known example of an enzyme that catalyses the formation of a non-aromatic, cyclic methylenolether. The enzyme was overexpressed in E. coli and the cell-free extracts were used in bioconversion experiments. Chemical synthesis gave access to a series of substrate surrogates that covered a broad structural space. Enzymatic assays revealed a broad substrate tolerance and high regioselectivity of JerF, which makes it an attractive candidate for an application in chemoenzymatic synthesis with particular usefulness for late stage application on 4-methoxy-5,6-dihydro-2H-pyran-2-one-containing natural products. View Full-Text
Keywords: methyltransferases; enzymes; chemoenzymatic synthesis; natural products; chemoselectivity; methylenolethers methyltransferases; enzymes; chemoenzymatic synthesis; natural products; chemoselectivity; methylenolethers
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Friedrich, S.; Hemmerling, F.; Lindner, F.; Warnke, A.; Wunderlich, J.; Berkhan, G.; Hahn, F. Characterisation of the Broadly-Specific O-Methyl-transferase JerF from the Late Stages of Jerangolid Biosynthesis. Molecules 2016, 21, 1443.

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