Journal ArticleDOI
Discovery of Key Dioxygenases that Diverged the Paraherquonin and Acetoxydehydroaustin Pathways in Penicillium brasilianum
Yudai Matsuda,Taiki Iwabuchi,Takayuki Fujimoto,Takayoshi Awakawa,Yu Nakashima,Takahiro Mori,Huiping Zhang,Fumiaki Hayashi,Ikuro Abe +8 more
TLDR
The biosynthetic gene cluster of 1 (the prh cluster) is identified and the pathway up to berkeleydione (2) is elucidated, which serves as the key intermediate for the biosynthesis of 1 as well as many other meroterpenoids.Abstract:
Paraherquonin (1), a fungal meroterpenoid produced by Penicillium brasilianum NBRC 6234, possesses a unique, highly congested hexacyclic molecular architecture. Here we identified the biosynthetic gene cluster of 1 (the prh cluster) and elucidated the pathway up to berkeleydione (2), which serves as the key intermediate for the biosynthesis of 1 as well as many other meroterpenoids. Interestingly, the nonheme iron and α-ketoglutarate-dependent dioxygenase PrhA constructs the cycloheptadiene moiety to afford 2 from preaustinoid A1 (6), probably via the homoallyl-homoallyl radical rearrangement. Additionally, another fungal strain, P. brasilianum MG11, which produces acetoxydehydroaustin instead of 1, was found to have a gene cluster nearly identical to the prh cluster. The dioxygenase encoded by the cluster shares 92% sequence identity with PrhA, and also accepts 6 but produces preaustinoid A3 (17) with a spiro-lactone system, generating a diverging point for the two different meroterpenoid pathways in the...read more
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Journal ArticleDOI
Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species
Jos Houbraken,Sándor Kocsubé,Cobus M. Visagie,Neriman Yilmaz,Xin-Cun Wang,Xin-Cun Wang,M. Meijer,Bart Kraak,Vit Hubka,K. Bensch,Robert A. Samson,Jens Christian Frisvad +11 more
TL;DR: The relationships between families and genera of the Eurotiales are re-evaluated using a nine-gene sequence dataset and an updated subgeneric, sectional and series classification for Aspergillus and Penicillium is introduced.
Journal ArticleDOI
Amazing Diversity in Biochemical Roles of Fe(II)/2-Oxoglutarate Oxygenases.
TL;DR: This review provides a general overview of recently characterized oxygenase reactions and their key biological roles, highlighting roles in controlling chromatin modification, transcription, mRNA demethylation, and mRNA splicing.
Journal ArticleDOI
Recent examples of α-ketoglutarate-dependent mononuclear non-haem iron enzymes in natural product biosyntheses.
TL;DR: Several novel αKG-NHFe enzymes involved in natural product biosyntheses discovered in recent years are summarized, including halogenation reactions, amino acid modifications and tailoring reactions in the biosynthesis of terpenes, lipids, fatty acids and phosphonates.
Journal ArticleDOI
Novofumigatonin biosynthesis involves a non-heme iron-dependent endoperoxide isomerase for orthoester formation.
Yudai Matsuda,Tongxuan Bai,Christopher B. W. Phippen,Christina Spuur Nødvig,Inge Kjærbølling,Tammi Camilla Vesth,Mikael Rørdam Andersen,Uffe Hasbro Mortensen,Charlotte Held Gotfredsen,Ikuro Abe,Thomas Ostenfeld Larsen +10 more
TL;DR: The elucidation of the biosynthetic pathway of novofumigatonin is elucidated and it is shown that the endoperoxidase NvfI and theendoperoxide isomerase N vfE are involved in it.
Journal ArticleDOI
Two Distinct Mechanisms for C–C Desaturation by Iron(II)- and 2-(Oxo)glutarate-Dependent Oxygenases: Importance of α-Heteroatom Assistance
N.P. Dunham,Wei-Chen Chang,Wei-Chen Chang,A.J. Mitchell,A.J. Mitchell,Ryan J. Martinie,Bo Zhang,Jonathan A. Bergman,Lauren J. Rajakovich,Lauren J. Rajakovich,Bo Wang,Alexey Silakov,Carsten Krebs,Amie K. Boal,J. Martin Bollinger +14 more
TL;DR: The results suggest that, although the sequential-HAT mechanism is feasible, its geometric requirements may make competing hydroxylation unavoidable, thus explaining the presence of α-heteroatoms in nearly all native substrates for Fe/2OG desaturases.
References
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Journal ArticleDOI
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