A role for old yellow enzyme in ergot alkaloid biosynthesis

Cheng, Johnathan Z.; Coyle, Christine M.; Panaccione, Daniel G.; O'Connor, Sarah E.

doi:10.1021/ja910193p

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A role for old yellow enzyme in ergot alkaloid biosynthesis

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Cheng, J. Z., Coyle, C. M., Panaccione, D. G., & O'Connor, S. E. (2010). A role for old yellow enzyme in ergot alkaloid biosynthesis. The Journal of Physical Chemistry B, 132(6), 1776-1777. doi:10.1021/ja910193p.

Cite as: https://hdl.handle.net/21.11116/0000-0002-AB4B-A

Abstract

Ergot alkaloids, secondary metabolites produced by filamentous fungi, elicit a diverse array of pharmacological effects. The biosynthesis of this class of natural products has not been fully elucidated. Here we demonstrate that a homologue of Old Yellow Enzyme encoded in the Aspergillus fumigatus ergot gene cluster catalyzes reduction of the alpha,beta unsaturated alkene of chanoclavine-1 aldehyde 3. This reduction, Which yields dihydrochanoclavine aldehyde, Facilitates an intramolecular reaction between a secondary amine and aldehyde to form the D ring of the ergot alkaloid structural framework.