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Key Documents

Safety Information

89377

Sigma-Aldrich

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:

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard 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

Regulatory Information

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Raisa N Krasikova et al.
Journal of medicinal chemistry, 54(1), 406-410 (2010-12-07)
There is a high demand for tumor specific PET tracers in oncology imaging. Besides glucose, certain amino acids also serve as energy sources and anabolic precursors for tumors. Therefore, (18)F-labeled amino acids are interesting probes for tumor specific PET imaging.
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)
J Galivan et al.
Advances in enzyme regulation, 23, 13-23 (1985-01-01)
Methotrexate is glutamylated in cultured hepatoma cells to derivatives that contain a total of 2 to 5 gamma-glutamyl residues. The rate of polyglutamate formation and extent of accumulation are saturable with respect to both medium concentration of methotrexate and time.
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)
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

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