Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 14, Pages 5816-5822Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201915486
Keywords
biosynthesis; Diels-Alder reactions; flavin-dependent monooxygenases; polyketides; sorbicillinoids
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Funding
- German Research Foundation (DFG) [INST 187/621-1, INST 187/686-1]
- DFG [CO 1328/5-1]
- Ministry of Higher Education of Egypt (MOHE)
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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 in 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 in vivo by SorD.
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