Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 5816-5822 |
| Seitenumfang | 7 |
| Fachzeitschrift | Angewandte Chemie |
| Jahrgang | 59 |
| Ausgabenummer | 14 |
| Frühes Online-Datum | 13 Jan. 2020 |
| Publikationsstatus | Veröffentlicht - 20 März 2020 |
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 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.
ASJC Scopus Sachgebiete
- Chemische Verfahrenstechnik (insg.)
- Katalyse
- Chemie (insg.)
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in: Angewandte Chemie , Jahrgang 59, Nr. 14, 20.03.2020, S. 5816-5822.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Diels–Alder reactions during the biosynthesis of sorbicillinoids
AU - Kahlert, Lukas
AU - Bassiony, Eman F.
AU - Cox, Russell J.
AU - Skellam, Elizabeth J.
N1 - Funding Information: This work was supported by the German Research Foundation (DFG, INST 187/621‐1, INST 187/686‐1). L.K. was funded by DFG (CO 1328/5‐1) and E.B. thanks the Ministry of Higher Education of Egypt (MOHE) for funding. Mary Shenouda is thanked for technical assistance.
PY - 2020/3/20
Y1 - 2020/3/20
N2 - 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.
AB - 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.
KW - biosynthesis
KW - Diels–Alder reactions
KW - flavin-dependent monooxygenases
KW - polyketides
KW - sorbicillinoids
UR - http://www.scopus.com/inward/record.url?scp=85078939627&partnerID=8YFLogxK
U2 - 10.1002/anie.201915486
DO - 10.1002/anie.201915486
M3 - Article
C2 - 31943627
AN - SCOPUS:85078939627
VL - 59
SP - 5816
EP - 5822
JO - Angewandte Chemie
JF - Angewandte Chemie
SN - 1433-7851
IS - 14
ER -