Ergot alkaloid biosynthesis in Aspergillus fumigatus: Conversion of chanoclavine-I aldehyde to festuclavine by the festuclavine synthase FgaFS in the presence of the old yellow enzyme FgaOx3

2010 ◽  
Vol 8 (15) ◽  
pp. 3500 ◽  
Author(s):  
Christiane Wallwey ◽  
Marco Matuschek ◽  
Xiu-Lan Xie ◽  
Shu-Ming Li
Keyword(s):  
Aspergillus Fumigatus ◽  
Ergot Alkaloid ◽  
Alkaloid Biosynthesis ◽  
Old Yellow Enzyme

scholarly journals Structure of anAspergillus fumigatusold yellow enzyme (EasA) involved in ergot alkaloid biosynthesis

2014 ◽  
Vol 70 (10) ◽  
pp. 1328-1332 ◽  
Author(s):  
Annemarie S. Chilton ◽  
Ashley L. Ellis ◽  
Audrey L. Lamb
Keyword(s):  
Crystal Structure ◽  
Amino Acids ◽  
Aspergillus Fumigatus ◽  
Ergot Alkaloid ◽  
Active Site ◽  
Self Regulation ◽  
Unsaturated Aldehyde ◽  
Asymmetric Unit ◽  
Alkaloid Biosynthesis ◽  
Old Yellow Enzyme

TheAspergillus fumigatusold yellow enzyme (OYE) EasA reduces chanoclavine-I aldehyde to dihydrochanoclavine aldehyde and works in conjunction with festuclavine synthase at the branchpoint for ergot alkaloid pathways. The crystal structure of the FMN-loaded EasA was determined to 1.8 Å resolution. The active-site amino acids of OYE are conserved, supporting a similar mechanism for reduction of the α/β-unsaturated aldehyde. The C-terminal tail of one monomer packs into the active site of a monomer in the next asymmetric unit, which is most likely to be a crystallization artifact and not a mechanism of self-regulation.

A bifunctional old yellow enzyme from Penicillium roqueforti is involved in ergot alkaloid biosynthesis

2017 ◽  
Vol 15 (38) ◽  
pp. 8059-8071 ◽  
Author(s):  
Nina Gerhards ◽  
Shu-Ming Li
Keyword(s):  
Ergot Alkaloid ◽  
Penicillium Roqueforti ◽  
Alkaloid Biosynthesis ◽  
Old Yellow Enzyme

Bifunctional FgaOx3Pr3catalyses the formation of festuclavine in the presence of EasG or FgaFS and enhances the activity of several chanoclavine-I dehydrogenases tremendously.

scholarly journals An Old Yellow Enzyme Gene Controls the Branch Point between Aspergillus fumigatus and Claviceps purpurea Ergot Alkaloid Pathways

2010 ◽  
Vol 76 (12) ◽  
pp. 3898-3903 ◽  
Author(s):  
Christine M. Coyle ◽  
Johnathan Z. Cheng ◽  
Sarah E. O'Connor ◽  
Daniel G. Panaccione
Keyword(s):  
Aspergillus Fumigatus ◽  
Ergot Alkaloid ◽  
Ergot Alkaloids ◽  
Aldehyde Group ◽  
Ring Structure ◽  
Ring Closure ◽  
Claviceps Purpurea ◽  
Wild Type ◽  
Old Yellow Enzyme ◽  
Clavicipitaceous Fungi

ABSTRACT Ergot fungi in the genus Claviceps and several related fungal groups in the family Clavicipitaceae produce toxic ergot alkaloids. These fungi produce a variety of ergot alkaloids, including clavines as well as lysergic acid derivatives. Ergot alkaloids are also produced by the distantly related, opportunistic human pathogen Aspergillus fumigatus. However, this fungus produces festuclavine and fumigaclavines A, B, and C, which collectively differ from clavines of clavicipitaceous fungi in saturation of the last assembled of four rings in the ergoline ring structure. The two lineages are hypothesized to share early steps of the ergot alkaloid pathway before diverging at some point after the synthesis of the tricyclic intermediate chanoclavine-I. Disruption of easA, a gene predicted to encode a flavin-dependent oxidoreductase of the old yellow enzyme class, in A. fumigatus led to accumulation of chanoclavine-I and chanoclavine-I-aldehyde. Complementation of the A. fumigatus easA mutant with a wild-type allele from the same fungus restored the wild-type profile of ergot alkaloids. These data demonstrate that the product of A. fumigatus easA is required for incorporation of chanoclavine-I-aldehyde into more-complex ergot alkaloids, presumably by reducing the double bond conjugated to the aldehyde group, thus facilitating ring closure. Augmentation of the A. fumigatus easA mutant with a homologue of easA from Claviceps purpurea resulted in accumulation of ergot alkaloids typical of clavicipitaceous fungi (agroclavine, setoclavine, and its diastereoisomer isosetoclavine). These data indicate that functional differences in the easA-encoded old yellow enzymes of A. fumigatus and C. purpurea result in divergence of their respective ergot alkaloid pathways.

A Role for Old Yellow Enzyme in Ergot Alkaloid Biosynthesis

2010 ◽  
Vol 132 (6) ◽  
pp. 1776-1777 ◽  
Author(s):  
Johnathan Z. Cheng ◽  
Christine M. Coyle ◽  
Daniel G. Panaccione ◽  
Sarah E. O’Connor
Keyword(s):  
Ergot Alkaloid ◽  
Alkaloid Biosynthesis ◽  
Old Yellow Enzyme

Probing ergot alkaloid biosynthesis: identification of advanced intermediates along the biosynthetic pathway

1988 ◽  
Vol 110 (6) ◽  
pp. 1970-1971 ◽  
Author(s):  
Alan P. Kozikowski ◽  
Jiang Ping. Wu ◽  
Masaaki. Shibuya ◽  
Heinz G. Floss
Keyword(s):  
Ergot Alkaloid ◽  
Biosynthetic Pathway ◽  
Alkaloid Biosynthesis
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