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Structural studies of FR96001M : a new antibacterial compound produced by Cyphellopsis anomalia TA96001

Berglund, Magnus (2001) KOK820 20001
Centre for Analysis and Synthesis
Abstract
FR96001M, (4R,5R)-4,5-Dihydroxy-5-((S)-1-hydroxy-heptyl)-cyclopent-2-enone, is a new antibacterial compound isolated from Cyphellopsis anomalia TA96001. Its structure was determined by spectroscopic methods. The absolute structure was determined with a FT-NMR version of Mosher´s method. FR96001 is very similar to the previously known antibacterial pentenomycins, wich is produced by Streptomyces eurythermus.
Derivatives to evaluate structure activity relationship were synthesized. The antibacterial and antifungal activity of new derivatives were tested on different species of bacteria and fungi. The results indicated that the double bond is essential for the activity, the tertiary hydroxyl group important for selectivity against bacteria... (More)
FR96001M, (4R,5R)-4,5-Dihydroxy-5-((S)-1-hydroxy-heptyl)-cyclopent-2-enone, is a new antibacterial compound isolated from Cyphellopsis anomalia TA96001. Its structure was determined by spectroscopic methods. The absolute structure was determined with a FT-NMR version of Mosher´s method. FR96001 is very similar to the previously known antibacterial pentenomycins, wich is produced by Streptomyces eurythermus.
Derivatives to evaluate structure activity relationship were synthesized. The antibacterial and antifungal activity of new derivatives were tested on different species of bacteria and fungi. The results indicated that the double bond is essential for the activity, the tertiary hydroxyl group important for selectivity against bacteria and the hydroxyl group in the carbon tail important for the activity. Synthetic routes to pentenomycins were found in the literature at least one of them could probably be modified and used to produce racemic FR96001. (Less)
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author
Berglund, Magnus
supervisor
organization
course
KOK820 20001
year
type
H1 - Master's Degree (One Year)
subject
keywords
organisk kemi, organic chemistry
language
English
id
3119317
date added to LUP
2012-09-28 16:07:46
date last changed
2015-12-14 13:31:00
@misc{3119317,
  abstract     = {FR96001M, (4R,5R)-4,5-Dihydroxy-5-((S)-1-hydroxy-heptyl)-cyclopent-2-enone, is a new antibacterial compound isolated from Cyphellopsis anomalia TA96001. Its structure was determined by spectroscopic methods. The absolute structure was determined with a FT-NMR version of Mosher´s method. FR96001 is very similar to the previously known antibacterial pentenomycins, wich is produced by Streptomyces eurythermus.
Derivatives to evaluate structure activity relationship were synthesized. The antibacterial and antifungal activity of new derivatives were tested on different species of bacteria and fungi. The results indicated that the double bond is essential for the activity, the tertiary hydroxyl group important for selectivity against bacteria and the hydroxyl group in the carbon tail important for the activity. Synthetic routes to pentenomycins were found in the literature at least one of them could probably be modified and used to produce racemic FR96001.},
  author       = {Berglund, Magnus},
  keyword      = {organisk kemi,organic chemistry},
  language     = {eng},
  note         = {Student Paper},
  title        = {Structural studies of FR96001M : a new antibacterial compound produced by Cyphellopsis anomalia TA96001},
  year         = {2001},
}