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Wiley, Angewandte Chemie International Edition, 17(54), p. 5117-5121, 2015

DOI: 10.1002/anie.201410002

Wiley, Angewandte Chemie, 17(127), p. 5206-5210, 2015

DOI: 10.1002/ange.201410002

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Discovery and Reconstitution of the Cycloclavine Biosynthetic Pathway—Enzymatic Formation of a Cyclopropyl Group**

Journal article published in 2015 by Dorota Jakubczyk, Lorenzo Caputi ORCID, Anaëlle Hatsch, Curt A. F. Nielsen, Melanie Diefenbacher, Jens Klein, Andrea Molt, Hartwig Schröder, Johnathan Z. Cheng, Michael Naesby, Sarah E. O'Connor
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Abstract

The ergot alkaloids, a class of fungal-derived natural products with important biological activities, are derived from a common intermediate, chanoclavine-I, which is elaborated into a set of diverse structures. Herein we report the discovery of the biosynthetic pathway of cycloclavine, a complex ergot alkaloid containing a cyclopropyl moiety. We used a yeast-based expression platform along with in vitro biochemical experiments to identify the enzyme that catalyzes a rearrangement of the chanoclavine-I intermediate to form a cyclopropyl moiety. The resulting compound, cycloclavine, was produced in yeast at titers of >500 mg L−1, thus demonstrating the feasibility of the heterologous expression of these complex alkaloids.