Ghent University Academic Bibliography

Advanced

Reactivity of N-(3-hydroxyacyl)amino acids and influence of their corresponding homoserine lactones on cyclic lipopeptide production

Ewout Ruysbergh UGent (2018)
abstract
In this PhD thesis isotope-labelled AHLs were synthesized which can be used as a tool to study the metabolization of AHLs. Secondly, the possible rearrangement of N-(3-hydroxyacyl)- L-homoserine lactones was investigated and proven to be very unlikely. This investigation resulted in the successful development of a synthetic entry toward 1,4-oxazepane-2,5-diones, which are extremely difficult to synthesize due to the presence of a lactam with a preference for the trans-conformation and a labile lactone moiety in one ring structure. By applying the disclosed methodology on the synthesis of the natural product serratin, the incorrect structural assignment of this compound was identified. Thirdly, the profound effect of a QS signal molecule, HO8, on the swarming behavior of Pseudomonas species CMR12a, was demonstrated. This influence goes presumably via an elegant fine-tuning of the ratio of the two produced CLPs, orfamide and sessilin via the control of orfamide production.
Please use this url to cite or link to this publication:
author
promoter
UGent, UGent and UGent
organization
alternative title
Reactiviteit van N-(3-hydroxyacyl)aminozuren en de invloed van de overeenkomstige homoserine lactonen op de productie van cyclische lipopeptiden
year
type
dissertation
publication status
published
subject
pages
VIII, 229 pages
publisher
Ghent University. Faculty of Bioscience Engineering
place of publication
Ghent, Belgium
defense location
Gent : Campus Coupure (lokaal E1.010)
defense date
2018-01-18 15:00
ISBN
9789463570695
language
English
UGent publication?
yes
classification
D1
copyright statement
I have retained and own the full copyright for this publication
id
8543529
handle
http://hdl.handle.net/1854/LU-8543529
date created
2018-01-03 20:12:08
date last changed
2018-01-15 12:10:17
@phdthesis{8543529,
  abstract     = {In this PhD thesis isotope-labelled AHLs were synthesized which can be used as a tool to study the metabolization of AHLs. Secondly, the possible rearrangement of N-(3-hydroxyacyl)- L-homoserine lactones was investigated and proven to be very unlikely. This investigation resulted in the successful development of a synthetic entry toward 1,4-oxazepane-2,5-diones, which are extremely difficult to synthesize due to the presence of a lactam with a preference for the trans-conformation and a labile lactone moiety in one ring structure. By applying the disclosed methodology on the synthesis of the natural product serratin, the incorrect structural assignment of this compound was identified. Thirdly, the profound effect of a QS signal molecule, HO8, on the swarming behavior of Pseudomonas species CMR12a, was demonstrated. This influence goes presumably via an elegant fine-tuning of the ratio of the two produced CLPs, orfamide and sessilin via the control of orfamide production.},
  author       = {Ruysbergh, Ewout},
  isbn         = { 9789463570695},
  language     = {eng},
  pages        = {VIII, 229},
  publisher    = {Ghent University. Faculty of Bioscience Engineering},
  school       = {Ghent University},
  title        = {Reactivity of N-(3-hydroxyacyl)amino acids and influence of their corresponding homoserine lactones on cyclic lipopeptide production},
  year         = {2018},
}

Chicago
Ruysbergh, Ewout. 2018. “Reactivity of N-(3-hydroxyacyl)amino Acids and Influence of Their Corresponding Homoserine Lactones on Cyclic Lipopeptide Production”. Ghent, Belgium: Ghent University. Faculty of Bioscience Engineering.
APA
Ruysbergh, E. (2018). Reactivity of N-(3-hydroxyacyl)amino acids and influence of their corresponding homoserine lactones on cyclic lipopeptide production. Ghent University. Faculty of Bioscience Engineering, Ghent, Belgium.
Vancouver
1.
Ruysbergh E. Reactivity of N-(3-hydroxyacyl)amino acids and influence of their corresponding homoserine lactones on cyclic lipopeptide production. [Ghent, Belgium]: Ghent University. Faculty of Bioscience Engineering; 2018.
MLA
Ruysbergh, Ewout. “Reactivity of N-(3-hydroxyacyl)amino Acids and Influence of Their Corresponding Homoserine Lactones on Cyclic Lipopeptide Production.” 2018 : n. pag. Print.