Controlling a structural branch point in ergot alkaloid biosynthesis

Cheng, Johnathan Z., Coyle, Christine M., Panaccione, Daniel G. and O'Connor, Sarah E. (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
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017)
Depositing User:	Rhiannon Harvey
Date Deposited:	21 Mar 2012 13:50
Last Modified:	10 Mar 2024 00:49
URI:	https://ueaeprints.uea.ac.uk/id/eprint/38400
DOI:	10.1021/ja105785p

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