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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:
2708-77-2
Molecular Weight:
165.12
Beilstein/REAXYS Number:
5254612
EC Number:
220-302-8
MDL number:
MFCD00055778
UNSPSC Code:
12352200
PubChem Substance ID:
57653342

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
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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
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)
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.
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
D W Konas et al.
The Journal of organic chemistry, 66(26), 8831-8842 (2001-12-26)
Electrophilic fluorination of enantiomerically pure 2-pyrrolidinones (4) derived from (L)-glutamic acid has been investigated as a method for the synthesis of single stereoisomers of 4-fluorinated glutamic acids. Reaction of the lactam enolate derived from 9 with NFSi results in a
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