DL-4-FluoroglutaMic acid
DL-4-FluoroglutaMic acid structure
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Common Name | DL-4-FluoroglutaMic acid | ||
|---|---|---|---|---|
| CAS Number | 2708-77-2 | Molecular Weight | 165.12000 | |
| Density | 1.498 g/cm3 | Boiling Point | 342.4ºC at 760 mmHg | |
| Molecular Formula | C5H8FNO4 | Melting Point | 185°C (dec.) | |
| MSDS | Chinese USA | Flash Point | 160.9ºC | |
| Symbol |
GHS07 |
Signal Word | Warning | |
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4-[18F]fluoroglutamic acid (BAY 85-8050), a new amino acid radiotracer for PET imaging of tumors: synthesis and in vitro characterization.
J. Med. Chem. 54(1) , 406-10, (2011) 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... |
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Mutations of the Corynebacterium glutamicum NCgl1221 gene, encoding a mechanosensitive channel homolog, induce L-glutamic acid production.
Appl. Environ. Microbiol. 73(14) , 4491-8, (2007) 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 secreti... |
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Vitamin K-dependent carboxylation. Study of the hydrogen abstraction stereochemistry with gamma-fluoroglutamic acid-containing peptides.
J. Biol. Chem. 258(13) , 7897-9, (1983) 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 occur... |
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Glutamylation of methotrexate in hepatoma cells in vitro: regulation and the development of specific inhibitors.
Adv. Enzyme Regul. 23 , 13-23, (1985) 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 methotrexa... |
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Bacterial defluorination of 4-fluoroglutamic acid.
Appl. Microbiol. Biotechnol. 77(3) , 699-703, (2007) 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 poten... |
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Electrophilic fluorination of pyroglutamic acid derivatives: application of substrate-dependent reactivity and diastereoselectivity to the synthesis of optically active 4-fluoroglutamic acids.
J. Org. Chem. 66(26) , 8831-42, (2001) 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 ... |
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DL-threo-4-fluoroglutamic acid. A chain-terminating inhibitor of folylpolyglutamate synthesis.
J. Biol. Chem. 260(11) , 6747-54, (1985) 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 tetrah... |
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Biochemical and biological properties of methotrexate analogs containing D-glutamic acid or D-erythro, threo-4-fluoroglutamic acid.
Biochem. Pharmacol. 42(12) , 2400-3, (1991)
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Effects of D,L-4-fluoroglutamic acid on glutamylation of methotrexate by hepatic cells in vitro.
Biochem. Pharmacol. 34(16) , 2995-7, (1985)
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Influence of stereoisomers of 4-fluoroglutamate on rat brain glutamate decarboxylase.
J. Enzym. Inhib. 15(3) , 273-82, (2000) 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 ... |