Controlling a Structural Branch Point in Ergot Alkaloid Biosynthesis

Cheng, JZ, Coyle, CM, Panaccione, DG and O'Connor, SE (2010) Controlling a Structural Branch Point in Ergot Alkaloid Biosynthesis. Journal of the American Chemical Society, 132 (37). pp. 12835-12837. ISSN 0002-7863

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Abstract

The ergot alkaloids are a diverse class of fungal-derived indole alkaloid natural products with potent pharmacological activities. The biosynthetic intermediate chanoclavine-I aldehyde 1 represents a branch point in ergot biosynthesis. Ergot alkaloids festuclavine 2 and agroclavine 3 derive from alternate enzymatic pathways originating from the common biosynthetic precursor chanoclavine-I aldehyde 1. Here we show that while the Old Yellow Enzyme homolog EasA from the ergot biosynthetic gene cluster of Aspergillus fumigatus acts on chanoclavine-I aldehyde 1 to yield festuclavine 2, EasA from Neotyphodium lolii, in contrast, produces agroclavine 3. Mutational analysis suggests a mechanistic rationale for the switch in activity that controls this critical branch point of ergot alkaloid biosynthesis.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
University of East Anglia > Faculty of Science > Research Groups > Synthetic Chemistry
Related URLs:
Depositing User: Rhiannon Harvey
Date Deposited: 21 Mar 2012 13:50
Last Modified: 25 Jul 2018 04:10
URI: https://ueaeprints.uea.ac.uk/id/eprint/38400
DOI: 10.1021/ja105785p

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