89377
4-Fluoro-DL-glutamic acid
≥93%
Synonym(s):
(±)-2-Amino-4-fluoroglutaric acid
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About This Item
Empirical Formula (Hill Notation):
C5H8FNO4
CAS Number:
Molecular Weight:
165.12
EC Number:
220-302-8
UNSPSC Code:
12352200
PubChem Substance ID:
Beilstein/REAXYS Number:
5254612
MDL number:
InChI key
JPSHPWJJSVEEAX-UHFFFAOYSA-N
InChI
1S/C5H8FNO4/c6-2(4(8)9)1-3(7)5(10)11/h2-3H,1,7H2,(H,8,9)(H,10,11)
SMILES string
NC(CC(F)C(O)=O)C(O)=O
assay
≥93%
form
solid
application(s)
peptide synthesis
Quality Level
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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J J McGuire et al.
The Journal of biological chemistry, 260(11), 6747-6754 (1985-06-10)
The effects of 4-fluoroglutamate on the reaction catalyzed by partially purified rat liver folylpolyglutamate synthetase have been investigated. DL-threo-4-Fluoroglutamate was an effective, concentration-dependent inhibitor of polyglutamylation of both tetrahydrofolate and methotrexate, while the erythro isomer was weakly inhibitory. 4-Fluoroglutamate acted
J Drsata et al.
Journal of enzyme inhibition, 15(3), 273-282 (2000-05-16)
Inhibition of rat brain glutamate decarboxylase (GAD, EC 4.1.1.15) by individual stereoisomers of 4-fluoroglutamate (4-F-Glu) and 2-fluoro-4-aminobutyrate (2-F-GABA) was studied. All stereoisomers of 4-F-Glu inhibited decarboxylation of L-glutamate catalysed by the enzyme preparation. At 1 x 10(-2) M concentration, the
Clár Donnelly et al.
Applied microbiology and biotechnology, 77(3), 699-703 (2007-09-29)
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
Biochemical and biological properties of methotrexate analogs containing D-glutamic acid or D-erythro, threo-4-fluoroglutamic acid.
J J McGuire et al.
Biochemical pharmacology, 42(12), 2400-2403 (1991-11-27)
Jun Nakamura et al.
Applied and environmental microbiology, 73(14), 4491-4498 (2007-05-22)
Corynebacterium glutamicum is a biotin auxotroph that secretes L-glutamic acid in response to biotin limitation; this process is employed in industrial L-glutamic acid production. Fatty acid ester surfactants and penicillin also induce L-glutamic acid secretion, even in the presence of
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