Options
Bacterial defluorination of 4-fluoroglutamic acid
Author(s)
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
Subject – LCSH
Amino acids
Organofluorine compounds
Bacteria
Language
English
Status of Item
Peer reviewed
This item is made available under a Creative Commons License
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
Mapped collections