dc.identifier.uri |
http://dx.doi.org/10.15488/12685 |
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dc.identifier.uri |
https://www.repo.uni-hannover.de/handle/123456789/12785 |
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dc.contributor.author |
De Mattos-Shipley, Kate M. J.
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|
dc.contributor.author |
Spencer, Catherine E.
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dc.contributor.author |
Greco, Claudio
|
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dc.contributor.author |
Heard, David M.
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dc.contributor.author |
O'Flynn, Daniel E.
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dc.contributor.author |
Dao, Trong T.
|
|
dc.contributor.author |
Song, Zhongshu
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dc.contributor.author |
Mulholland, Nicholas P.
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dc.contributor.author |
Vincent, Jason L.
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dc.contributor.author |
Simpson, Thomas J.
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dc.contributor.author |
Cox, Russell J.
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dc.contributor.author |
Bailey, Andrew M.
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dc.contributor.author |
Willis, Christine L.
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dc.date.accessioned |
2022-08-24T11:37:57Z |
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dc.date.available |
2022-08-24T11:37:57Z |
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dc.date.issued |
2020 |
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dc.identifier.citation |
De Mattos-Shipley, K.M.J.; Spencer, C.E.; Greco, C.; Heard, D.M.; O'Flynn, D.E. et al.: Uncovering biosynthetic relationships between antifungal nonadrides and octadrides. In: Chemical Science 11 (2020), Nr. 42, S. 11570-11578. DOI: https://doi.org/10.1039/d0sc04309e |
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dc.description.abstract |
Maleidrides are a class of bioactive secondary metabolites unique to filamentous fungi, which contain one or more maleic anhydrides fused to a 7-, 8- or 9- membered carbocycle (named heptadrides, octadrides and nonadrides respectively). Herein structural and biosynthetic studies on the antifungal octadride, zopfiellin, and nonadrides scytalidin, deoxyscytalidin and castaneiolide are described. A combination of genome sequencing, bioinformatic analyses, gene disruptions, biotransformations, isotopic feeding studies, NMR and X-ray crystallography revealed that they share a common biosynthetic pathway, diverging only after the nonadride deoxyscytalidin. 5-Hydroxylation of deoxyscytalidin occurs prior to ring contraction in the zopfiellin pathway of Diffractella curvata. In Scytalidium album, 6-hydroxylation-confirmed as being catalysed by the α-ketoglutarate dependent oxidoreductase ScyL2-converts deoxyscytalidin to scytalidin, in the final step in the scytalidin pathway. Feeding scytalidin to a zopfiellin PKS knockout strain led to the production of the nonadride castaneiolide and two novel ring-open maleidrides. © The Royal Society of Chemistry. |
eng |
dc.language.iso |
eng |
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dc.publisher |
Cambridge : RSC |
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dc.relation.ispartofseries |
Chemical Science 11 (2020), Nr. 42 |
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dc.rights |
CC BY 4.0 Unported |
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dc.rights.uri |
https://creativecommons.org/licenses/by/4.0/ |
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dc.subject |
Biosynthesis |
eng |
dc.subject |
Metabolites |
eng |
dc.subject |
Bioinformatic analysis |
eng |
dc.subject |
Biosynthetic pathway |
eng |
dc.subject |
Filamentous fungi |
eng |
dc.subject |
Gene disruptions |
eng |
dc.subject |
Genome sequencing |
eng |
dc.subject |
Knockout strains |
eng |
dc.subject |
Ring contraction |
eng |
dc.subject |
Secondary metabolites |
eng |
dc.subject |
X-ray crystallography |
eng |
dc.subject.ddc |
540 | Chemie
|
ger |
dc.title |
Uncovering biosynthetic relationships between antifungal nonadrides and octadrides |
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dc.type |
Article |
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dc.type |
Text |
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dc.relation.essn |
2041-6539 |
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dc.relation.issn |
2041-6520 |
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dc.relation.doi |
https://doi.org/10.1039/d0sc04309e |
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dc.bibliographicCitation.issue |
42 |
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dc.bibliographicCitation.volume |
11 |
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dc.bibliographicCitation.firstPage |
11570 |
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dc.bibliographicCitation.lastPage |
11578 |
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dc.description.version |
publishedVersion |
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tib.accessRights |
frei zug�nglich |
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