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  5. Bacterial defluorination of 4-fluoroglutamic acid
 
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Bacterial defluorination of 4-fluoroglutamic acid

Author(s)
Donnelly, Clár  
Murphy, Cormac D.  
Uri
http://hdl.handle.net/10197/3781
Date Issued
2007
Date Available
2012-09-04T15:44:28Z
Abstract
Fluorinated amino acids are used as enzyme inhibitors, mechanistic probes and in the production of pharmacologically active peptides. Because enantiomerically pure 4-fluoroglutamate is difficult to prepare, the selective degradation of the l-isomer is a potentially convenient method of obtaining d-4-fluoroglutamate from the racemate. In this paper, we describe our investigations on the degradation of 4-fluoroglutamate by bacteria. Fluoride ion was detected in resting-cell cultures of a number of bacteria that were incubated with racemic 4-fluoroglutamate. Analysis of the culture supernatants by chiral gas chromatography–mass spectrometry revealed that only the l-isomer was degraded. The degradation of 4-fluoroglutamate was also examined in cell-free extracts of Streptomyces cattleya and Proteus mirabilis, and it was observed that equimolar concentrations of fluoride ion and ammonia were generated. The activity was located in the soluble fraction of cell extracts, thus is not related to the l-2-amino-4-chloro-4-pentenoic acid dehydrochlorinase previously identified in membrane fractions of P. mirabilis.
Sponsorship
Other funder
Other Sponsorship
Enterprise Ireland
Type of Material
Journal Article
Publisher
Springer
Journal
Applied microbiology and biotechnology
Volume
77
Issue
3
Start Page
699
End Page
703
Copyright (Published Version)
2007 Springer-Verlag
Subjects

Dehalogenation

Amino acid

Bacteria

Subject – LCSH
Amino acids
Organofluorine compounds
Bacteria
DOI
10.1007/s00253-007-1200-9
Language
English
Status of Item
Peer reviewed
This item is made available under a Creative Commons License
https://creativecommons.org/licenses/by-nc-sa/1.0/
File(s)
No Thumbnail Available
Name

Defluorination text revision.doc

Description
Text
Size

57 KB

Format

Microsoft Word

Checksum (MD5)

b7e61337bdd68ed8f7139cad4258e657

No Thumbnail Available
Name

Defluorination figures revision.doc

Description
Figures
Size

582.5 KB

Format

Microsoft Word

Checksum (MD5)

ca9b09264b053492bdba6fbfc818f25a

Owning collection
Biomolecular and Biomedical Science Research Collection
Mapped collections
CSCB Research Collection

Item descriptive metadata is released under a CC-0 (public domain) license: https://creativecommons.org/public-domain/cc0/.
All other content is subject to copyright.

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