Details
| Original language | English |
|---|---|
| Qualification | Doctor rerum naturalium |
| Awarding Institution | |
| Supervised by |
|
| Date of Award | 23 Aug 2018 |
| Place of Publication | Hannover |
| Publication status | Published - 2018 |
Abstract
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Hannover, 2018. 186 p.
Research output: Thesis › Doctoral thesis
}
TY - BOOK
T1 - The biosynthesis of phyllostictine A and Sch-642305 from Phyllosticta cirsii and Phomopsis CMU-LMA
AU - Trenti, Francesco
N1 - Doctoral thesis
PY - 2018
Y1 - 2018
N2 - The presented work focuses on the biosynthesis of fungal natural products. Structural analysis of phyllostictine A revealed the literature structure to be erroneous and led to the revised bicyclic 3-methylene tetramic acid. In particular, feeding 13 C-labeled precursors showed a haphazard incorporation into and set the basis for the correct structure elucidation. The Biosynthetic Gene Cluster (BGC) was identified by total genome sequencing of the producer (P. cirsii ) and in silico analyis. Targeted knock out experiments confirmed the BGC to be involved in phyllostictine A biosynthesis and produced an intermediate. In the attempt to define each biosynthetic step that takes part in Sch-642305 biosynthesis, two intermediates were observed after targeted knock out of a cytochrome P450 cytochrome and a flavoprotein oxidase, respectively. Genome assembly and in silico analysis showed over 150 BGC for this strain. The sch-related BGC was defined by rational survey and homology comparison with other producing organisms, such as Penicillium verrucosum and Penicillium brefeldianum, producers of Sch-642305 and Brefeldin A respectively. Although, other genes of Sch-642305 cluster were successfully disrupted, no other intermediate was observed.
AB - The presented work focuses on the biosynthesis of fungal natural products. Structural analysis of phyllostictine A revealed the literature structure to be erroneous and led to the revised bicyclic 3-methylene tetramic acid. In particular, feeding 13 C-labeled precursors showed a haphazard incorporation into and set the basis for the correct structure elucidation. The Biosynthetic Gene Cluster (BGC) was identified by total genome sequencing of the producer (P. cirsii ) and in silico analyis. Targeted knock out experiments confirmed the BGC to be involved in phyllostictine A biosynthesis and produced an intermediate. In the attempt to define each biosynthetic step that takes part in Sch-642305 biosynthesis, two intermediates were observed after targeted knock out of a cytochrome P450 cytochrome and a flavoprotein oxidase, respectively. Genome assembly and in silico analysis showed over 150 BGC for this strain. The sch-related BGC was defined by rational survey and homology comparison with other producing organisms, such as Penicillium verrucosum and Penicillium brefeldianum, producers of Sch-642305 and Brefeldin A respectively. Although, other genes of Sch-642305 cluster were successfully disrupted, no other intermediate was observed.
U2 - 10.15488/3649
DO - 10.15488/3649
M3 - Doctoral thesis
CY - Hannover
ER -