32563-24-9

Usage

Uses

Used in Pharmaceutical Development:
L-ERYTHRO-4-FLUOROGLUTAMIC ACID is used as a key compound in the development of pharmaceutical drugs, specifically for neurological disorders and psychiatric conditions. Its unique structure allows it to interact with glutamate receptors, offering a novel approach to treating these conditions.
Used in Research:
L-ERYTHRO-4-FLUOROGLUTAMIC ACID is utilized as a research tool for studying the role of glutamate receptors in various physiological and pathological processes. Its specific chemical properties make it valuable for understanding receptor functions and their implications in health and disease.
Used in Neurological Applications:
In the field of neurology, L-ERYTHRO-4-FLUOROGLUTAMIC ACID is used as a therapeutic agent for targeting neurological disorders. Its interaction with glutamate receptors can potentially lead to the development of treatments that modulate neurotransmission and alleviate symptoms associated with these disorders.
Used in Psychiatric Applications:
L-ERYTHRO-4-FLUOROGLUTAMIC ACID is employed as a pharmaceutical agent for psychiatric conditions. Its ability to modulate glutamate receptor activity may contribute to the development of new treatments for mental health disorders, offering alternative approaches to existing therapies.

InChI:InChI=1/C5H8FNO4/c6-2(4(8)9)1-3(7)5(10)11/h2-3H,1,7H2,(H,8,9)(H,10,11)/t2-,3-/m0/s1

Upstream product

• 149033-38-5 Methyl 1-acetyl-trans-4-fluoro-D-pyrrolidin-5-one-2-carboxylate 
• 91307-51-6 L-leucyl-D,L-(threo+erythro)-γ-fluoroglutamate 
• 91307-56-1 L-leucyl-L-erythro-γ-fluoroglutamate 
• 393810-25-8 (2S,4R)-4-fluoro-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 2358-03-4 erythro-4-fluoroglutamic acid 5-methyl ester 
• 78804-96-3 (2S,4S)-1-acetyl-4-hydroxyproline methyl ester 
• 132651-95-7 N-acetyl-4(R)-fluoro-L-proline methyl ester 
• 67943-19-5 methyl (2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylate 
• 2708-77-2 D,L-erythro,threo-4-fluoroglutamic acid 
• 618-27-9 hydroxy L-proline 
• 51-35-4 4R-4-hydroxyproline 
• 64187-47-9 1-benzyloxycarbonyl-4-keto-L-proline 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 

Relevant academic research and scientific papers

[F-18]-labeled L-glutamic acid, [F-18]-labeled L-glutamine, derivatives thereof and use thereof and processes for their preparation

The compounds and the synthesis of [F-18]-labeled L-glutamic acid, [F-18]-labeled L-glutamate, their derivatives as set forth in formula (I) and their uses are described.

[F-18]-LABELED L-GLUTAMIC ACID, [F-18]-LABELED L-GLUTAMINE, DERIVATIVES THEREOF AND USE THEREOF AND PROCESSES FOR THEIR PREPARATION

The compounds and the synthesis of [F-18]-labeled L-glutamic acid, [F-18]-labeled L-glutamate, their derivatives as set forth in formula (I) and their uses are described.

[F-18]-LABELED L-GLUTAMIC ACID, [F-18]-LABELED L-GLUTAMINE, DERIVATIVES THEREOF AND USE THEREOF AND PROCESSES FOR THEIR PREPARATION

The compounds and the synthesis of [F-18]-labeled L-glutamic acid, [F-18]-labeled L-glutamate, their derivatives as set forth in formula (I) and their uses are described.

Electrophilic fluorination of pyroglutamic acid derivatives: Application of substrate-dependent reactivity and diastereoselectivity to the synthesis of optically active 4-fluoroglutamic acids

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 completely diastereoselective monofluorination reaction to yield the monocyclic trans-substituted α-fluoro lactam product 21. Unfortunately, a decreased kinetic acidity in 21 and other structurally related monofluorinated products renders them resistant to a second fluorination. In contrast, the bicyclic lactam 12 is readily difluorinated under the standard conditions described to yield the α,α-difluoro lactam 24. The difference in reactivity between the two types of related lactams is attributed mainly to the presence or lack of a steric interaction between the base used for deprotonation and the protecting group present in the pyrrolidinone substrates. This conclusion was reached based on analysis of the X-ray crystal structure of 21, molecular modeling, and experimental evidence. The key intermediates 21 and 24 are converted to (2S,4R)-4-fluoroglutamic acid and (2S)-4,4-difluoroglutamic acid, respectively.

Practical synthesis of L-erythro- and L-threo-4-fluoroglutamic acids using aminoacylase

Enantiomerically pure L-erythro- and L-threo-4-fluoroglutamic acids 1a and 1b were conveniently prepared. The key steps in this synthesis relied upon separation of diastereomers of N-chloroacetyl-4-fluoroglutamic acid 5-methyl ester 7 by recrystallization and enzymatic resolution of enantiomers of the resulting 7(a+c) and 7(b+d) by aminoacylase. Protection of the γ-carboxyl group as a methyl ester was found to be crucial for this enzymatic reaction.

Stereospecific syntheses of all four stereoisomers of 4-fluoroglutamic acid

(+)-L-threo-4-fluoroglutamic acid . (-)-D-threo-4-Fluoroglutamic acid was prepared analogously from trans-4-hydroxy-D-proline, obtained from its diastereomer by inversion of configuration at carbon 4 of the pyrrolidine ring using the diethyl azodicarboxylate-triphenylphosphine procedure. cis-4-Hydroxy-L-proline, necessary for the synthesis of (+)-L-erythro-4-fluoroglutamic acid , was prepared from trans-4-hydroxy-L-proline by benzyloxycarbonylation at the nitrogen, oxidation of the 1-benzyloxycarbonyl-trans-4-hydroxy-L-proline to 1-benzyloxycarbonyl-4-oxo-L-proline, its reduction to 1-benzyloxycarbonyl-cis-4-hydroxy-L-proline and deprotection of the latter at the nitrogen. (-)-cis-4-Fluoro-L-proline and (+)-trans-4-fluoro-D-proline were isolated after the hydrolysis of incompletely oxidized methyl 1-acetyl-cis-4-fluoro-L-prolinate and methyl 1-acetyl-trans-4-fluoro-D-prolinate, respectively.

Resolution of γ-Methyl and γ-Fluoroglutamic Acids. Lack of Stereospecificity of Leucine Aminopeptidase with L-Leucyl-L-erythro-γ-substituted Glutamates

The hydrolysis of L-leucyl-γ-substituted D,L-glutamates by leucine aminopeptidase, from porcine kidney, is stereospecific with threo-γ-methyl and threo-γ-fluoroglutamate containing dipeptides whereas there is a lack of stereospecificity with erythro-isomers.The optical purities of L-threo- and L-erythro-glutamate isomers thus obtained have been monitored by gas chromatography, high pressure liquid chromatography, or nuclear magnetic resonance.The optical rotations of optically pure L-isomers have been measured and the discrepancies with former publications are discussed.