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
Beilstein:
5254612
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
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Quality Level
Assay
≥93%
form
solid
application(s)
peptide synthesis
SMILES string
NC(CC(F)C(O)=O)C(O)=O
InChI
1S/C5H8FNO4/c6-2(4(8)9)1-3(7)5(10)11/h2-3H,1,7H2,(H,8,9)(H,10,11)
InChI key
JPSHPWJJSVEEAX-UHFFFAOYSA-N
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
Effects of D,L-4-fluoroglutamic acid on glutamylation of methotrexate by hepatic cells in vitro.
J Galivan et al.
Biochemical pharmacology, 34(16), 2995-2997 (1985-08-15)
Stereoisomers of 4-fluoroglutamic acid: influence on Escherichia coli glutamate decarboxylase.
J Drsata et al.
Die Pharmazie, 54(9), 713-714 (1999-10-16)
J Dubois et al.
The Journal of biological chemistry, 258(13), 7897-7899 (1983-07-10)
Two pentapeptides Phe-Leu-X-Glu-Val where X is either the L-threo-gamma-fluoroglutamic acid or the L-erythro-isomer have been synthesized and tested as substrates in the vitamin K-dependent carboxylation. Both peptides are carboxylated, but the reaction occurs exclusively on the glutamic acid of the
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