dc.identifier.uri |
http://dx.doi.org/10.15488/10638 |
|
dc.identifier.uri |
https://www.repo.uni-hannover.de/handle/123456789/10716 |
|
dc.contributor.author |
Zhang, Haili
|
|
dc.contributor.author |
Hantke, Verena
|
|
dc.contributor.author |
Bruhnke, Pia
|
|
dc.contributor.author |
Skellam, Elizabeth J.
|
|
dc.contributor.author |
Cox, Russell J.
|
|
dc.date.accessioned |
2021-03-26T08:44:48Z |
|
dc.date.available |
2021-03-26T08:44:48Z |
|
dc.date.issued |
2020 |
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dc.identifier.citation |
Zhang, H.; Hantke, V.; Bruhnke, P.; Skellam, E.J.; Cox, R.J.: Chemical and Genetic Studies on the Formation of Pyrrolones During the Biosynthesis of Cytochalasans. In: Chemistry - A European Journal 27 (2020), Nr. 9, S. 3106-3113. DOI: https://doi.org/10.1002/chem.202004444 |
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dc.description.abstract |
A key step during the biosynthesis of cytochalasans is a proposed Knoevenagel condensation to form the pyrrolone core, enabling the subsequent 4+2 cycloaddition reaction that results in the characteristic octahydroisoindolone motif of all cytochalasans. In this work, we investigate the role of the highly conserved a,ß-hydrolase enzymes PyiE and ORFZ during the biosynthesis of pyrichalasin H and the ACE1 metabolite, respectively, using gene knockout and complementation techniques. Using synthetic aldehyde models we demonstrate that the Knoevenagel condensation proceeds spontaneously but results in the 1,3-dihydro-2H-pyrrol-2-one tautomer, rather than the required 1,5-dihydro-2H-pyrrol-2-one tautomer. Taken together our results suggest that the a,ß-hydrolase enzymes are essential for first ring cyclisation, but the precise nature of the intermediates remains to be determined. © 2020 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH |
eng |
dc.language.iso |
eng |
|
dc.publisher |
Weinheim : Wiley-VCH Verl. |
|
dc.relation.ispartofseries |
Chemistry - A European Journal 27 (2020), Nr. 9 |
|
dc.rights |
CC BY-NC 4.0 Unported |
|
dc.rights.uri |
https://creativecommons.org/licenses/by-nc/4.0/ |
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dc.subject |
biosynthesis |
eng |
dc.subject |
cytochalasan |
eng |
dc.subject |
hydrolase |
eng |
dc.subject |
Knoevenagel |
eng |
dc.subject |
pyrrolone |
eng |
dc.subject.ddc |
540 | Chemie
|
ger |
dc.title |
Chemical and Genetic Studies on the Formation of Pyrrolones During the Biosynthesis of Cytochalasans |
|
dc.type |
Article |
|
dc.type |
Text |
|
dc.relation.essn |
1521-3765 |
|
dc.relation.issn |
0947-6539 |
|
dc.relation.doi |
https://doi.org/10.1002/chem.202004444 |
|
dc.bibliographicCitation.issue |
9 |
|
dc.bibliographicCitation.volume |
27 |
|
dc.bibliographicCitation.firstPage |
3106 |
|
dc.bibliographicCitation.lastPage |
3113 |
|
dc.description.version |
publishedVersion |
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tib.accessRights |
frei zug�nglich |
|