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Angew Chem Weinheim Bergstr Ger. 2015 Apr 20;127(17):5206-5210. Epub 2015 Feb 25.

Discovery and Reconstitution of the Cycloclavine Biosynthetic Pathway-Enzymatic Formation of a Cyclopropyl Group.

Author information

1
Department of Biological Chemistry, John Innes Centre, Colney Lane, Norwich (UK).
2
Evolva SA, Duggingerstrasse 23, Reinach (Switzerland).
3
BASF SE, GVF/D-A030, Ludwigshafen (Germany).

Abstract

in English, German

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.

KEYWORDS:

Biosynthese; Cyclopropane; Mutterkornalkaloide; Naturstoffe; Rekonstitution

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