Diels-Alder Reactions During the Biosynthesis of Sorbicillinoids.
Angew Chem Int Ed Engl
; 59(14): 5816-5822, 2020 03 27.
Article
em En
| MEDLINE
| ID: mdl-31943627
ABSTRACT
The sorbicillinoids are a class of biologically active and structurally diverse fungal polyketides arising from sorbicillin. Through co-expression of sorA, sorB, sorC, and sorD from Trichoderma reesei QM6a, the biosynthetic pathway to epoxysorbicillinol and dimeric sorbicillinoids, which resemble Diels-Alder-like and Michael-addition-like products, was reconstituted in Aspergillus oryzae NSAR1. Expression and feeding experiments demonstrated the crucial requirement of the flavin-dependent monooxygenase SorD for the formation of dimeric sorbicillinoids, hybrid sorbicillinoids, and epoxysorbicillinol inâ
vivo. In contrast to prior reports, SorD catalyses neither the oxidation of 2',3'-dihydrosorbicillin to sorbicillin nor the oxidation of sorbicillinol to oxosorbicillinol. This is the first report that both the intermolecular Diels-Alder and Michael dimerization reactions, as well as the epoxidation of sorbicillinol are catalysed inâ
vivo by SorD.
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01-internacional
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MEDLINE
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Cicloexanonas
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En
Ano de publicação:
2020
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Article