402821-16-3

Usage

Uses

Used in Biochemical Research:
(4R)-4-Benzyl-D-glutamic acid is used as a research compound for studying various biochemical processes and mechanisms. Its unique structure and properties make it a valuable tool in understanding the role of amino acids in biological systems.
Used in Peptide Synthesis:
In the field of peptide synthesis, (4R)-4-Benzyl-D-glutamic acid is used as a building block for creating novel peptides with potential applications in drug development and therapeutics. Its distinct stereochemistry allows for the exploration of new peptide structures and their interactions with biological targets.
Used in Protein Synthesis:
(4R)-4-Benzyl-D-glutamic acid is used as a component in the synthesis of modified proteins, which can be employed in research to investigate the effects of amino acid modifications on protein structure, function, and stability.
Used in Enzymatic Reactions:
(4R)-4-BENZYL-D-GLUTAMIC ACID is used in enzymatic reactions to study the role of amino acids in enzyme catalysis and to develop new enzymes with altered substrate specificity or improved catalytic efficiency.
Used in Neurotransmission Research:
As a derivative of glutamic acid, (4R)-4-Benzyl-D-glutamic acid is used in research to understand its potential role in neurotransmission in the central nervous system, which could lead to insights into neurological disorders and the development of new therapeutic strategies.

InChI:InChI=1/C12H15NO4/c13-10(12(16)17)7-9(11(14)15)6-8-4-2-1-3-5-8/h1-5,9-10H,6-7,13H2,(H,14,15)(H,16,17)/t9-,10-/m1/s1

Upstream product

• 153080-92-3 ethyl (2S,4S)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate 
• 171038-44-1 (S)-5-Oxo-4-[1-phenyl-meth-(E)-ylidene]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 81658-26-6 tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate 
• 100-39-0 benzyl bromide 
• 474024-64-1 ethyl (2R,4S)-N-BOC-4-benzyl pyroglutamate 
• 144978-12-1 1-tert-butyl 2-ethyl (2R)-5-oxopyrrolidine-1,2-dicarboxylate 
• 129413-81-6 (2R,4S)-2-Benzyl-4-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid 
• 129413-78-1 5(S)-((t-butyl-dimethyl-silyloxy)methyl)-3(R)-phenylmethyl-N-BOC-2-pyrrolidinone 
• 129413-84-9 (2R,4S)-2-Benzyl-4-tert-butoxycarbonylamino-5-hydroxy-pentanoic acid methyl ester 
• 129413-87-2 (2R,4S)-2-Benzyl-4-tert-butoxycarbonylamino-5-hydroxy-pentanoic acid 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 4931-66-2 methyl (S)-pyroglutamate 
• 108963-96-8 (S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one 
• 174678-99-0 dimethyl 2-oxo-4-(phenylmethyl)glutarate 

Downstream Products

• 26845-84-1 γ-benzyl-glutamic acid N-carboxyanhydride 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of glutamic acid analogues: Substrate specificity and synthetic applications of branched chain aminotransferase from Escherichia coli

(Chemical Equation Presented) A new route to α-keto acids is described, based on the ozonolysis of enol acetates obtained from α-substituted β-keto esters. Escherichia coli branched chain aminotransferase (BCAT) activity toward a variety of substituted 2-oxoglutaric acids was demonstrated analytically. BCAT was shown to have a broad substrate spectrum, complementary to that of aspartate aminotransferase, and to offer access to a variety of glutamic acid analogues. The usefulness of BCAT was demonstrated through the synthesis of several 3- and 4-substituted derivatives.

Chemoenzymatic synthesis of a series of 4-substituted glutamate analogues and pharmacological characterization at human glutamate transporters subtypes 1-3

A series of nine L-2,4-s;yrc-4-alkylglutamic acid analogues (1a-i) were synthesized in high yield and high enantiomeric excess (>99% ee) from their corresponding 4-substituted ketoglutaric acids (2a-i), using the enzyme aspartate aminotransferase (AAT) from pig heart or E. coli. The synthesized compounds were evaluated as potential ligands for the glutamate transporters EAAT1, EAAT2, and EAAT3 (excitatory amino acid transporter, subtypes 1-3) in the FLIPR membrane potential (FMP) assay. We found a distinct change in the pharmacological profile when the 4-methyl group (compound 1a, an EAAT1 substrate and EAAT2,3 inhibitor) was extended to a 4-ethyl group, compound 1b, as this analogue is an inhibitor at all three subtypes, EAAT1-3. Furthermore, we conclude that both large and bulky hydrophobic substituents in the 4-position of L-2,4-syn Glu are allowed by all three glutamate transporter subtypes EAAT1-3 while maintaining inhibitory activity.

Monatin, its stereoisomers and derivatives: Modeling the sweet taste chemoreception mechanism

The sweet natural compound monatin 1 has two stereogenic centers, and the 2S,4S absolute configuration has been attributed previously to the natural isomer. Among the four stereoisomers of monatin, three of them, particularly the 2R,4R isomer, tastes intensely sweet. The conformations of the four compounds have been studied by means of molecular modelling techniques. Both the diastereoisomeric forms show strong intramolecular hydrogen bonds which involve different functional groups and give rise to two different minimum energy conformations. The tertiary alcohol group in monatin seems to be indirectly involved in the generation of the taste, acting as an important contraint in generating the active conformation. The most important glucophores have been identified in the terminal -NH3+ and -COO - groups and in the indole ring by comparison with known topological models of sweet compounds and through the synthesis of appropriate derivatives in which some of these groups are lacking or modified. The relative affinity of each stereoisomer for its putative sweet taste receptor has been estimated semi-quantitatively with the pseudoreceptor modelling technique. The predicted activity calculated with this technique is in good agreement with the experimental data and explains why the 2R,4R isomer (and not the natural 2S,4S isomer) is the sweetest of the series. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

4-Substituted D-glutamic acid analogues: The first potent inhibitors of glutamate racemase (MurI) enzyme with antibacterial activity

The first potent inhibitors of glutamate racemase (MurI) enzyme that show whole cell antibacterial activity are described. Optically pure 4-substituted D-glutamic acid analogues with (2R,4S) stereochemistry and bearing aryl-, heteroaryl-, cinnamyl-, or biaryl-methyl substituents represent a novel class of glutamate racemase inhibitors. Exploration of the D-Glu core led to the identification of lead compounds (-)-8 and 10. 2-Naphthylmethyl derivative 10 was found to be a potent competitive inhibitor of glutamate racemase activity (Ki = 16 nM, circular dichroism assay; IC50 = 0.1 μg/mL high-performance liquid chromatography (HPLC) assay). Thorough structure-activity relationship (SAR) studies led to benzothienyl derivatives such as 69 and 74 with increased potency (IC50 = 0.036 and 0.01 μg/mL, respectively, HPLC assay). These compounds showed potent whole cell antibacterial activity against S. pneumoniae PN-R6, and good correlation with the enzyme assay. Compounds 69, 74 and biaryl derivative 52 showed efficacy in an in vivo murine thigh infection model against Streptococcus pneumoniae. Data described herein suggest that glutamate racemase may be a viable target for developing new antibacterial agents.

(2S,3S)-2-Amino-3-(2,2-diphenylethyl)pentanedioic acid selective group 2 metabotropic glutamate receptor antagonist

(2S,4S)-2-Amino-4-(4,4-diphenylbut-1-yl)-pentane-1,5-dioic acid 1m, is a novel metabotropic glutamate receptor (mGluR) antagonist with insignificant ionotropic affinity. It is a selective antagonist of negatively-coupled cAMP-linked mGluRs with no effect

SYNTHESES OF (2S,4S)- AND (2S,4R)-4-SUBSTITUTED GLUTAMIC ACID ANALOGUES FOR NEUROEXCITATORY ACTIVITY STUDIES

The stereospecific syntheses of various lenght of 4(R)- and 4(S)-substituted 2(S)-glutamic acid were described.