1499-55-4

Basic information

• Product Name: L-Glutamic acid 5-methyl ester
• Synonyms: 5-METHYL L-GLUTAMATE;L-GLUTAMIC ACID 5-METHYL ESTER;L-GLUTAMIC ACID GAMMA-METHYL ESTER;L-GLUTAMIC ACID, G-METHYL ESTER;H-L-GLU(ME)-OH;H-GLU(OME)-OH;GAMMA-L-GLU-METHYL ESTER;GAMMA-METHYL-L-GLUTAMATE
• CAS NO: 1499-55-4
• Molecular Formula: C₆H₁₁NO₄
• Molecular Weight: 161.16
• EINECS: 216-110-9
• Product Categories: Amino Acids Derivatives;Glutamic acid [Glu, E];Amino Acids and Derivatives;Pyrazoles
• Mol File: 1499-55-4.mol

Chemical Properties

• Melting Point: 182 °C (dec.)(lit.)
• Boiling Point: 287.44°C (rough estimate)
• Flash Point: 145 °C
• Appearance: white amorphous powder
• Density: 1.3482 (rough estimate)
• Vapor Pressure: 0.000217mmHg at 25°C
• Refractive Index: 29 ° (C=2, 6mol/L HCl)
• Storage Temp.: 2-8°C
• PKA: 2.18±0.10(Predicted)
• Water Solubility: Soluble in water
• BRN: 1725252
• CAS DataBase Reference: L-Glutamic acid 5-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Glutamic acid 5-methyl ester(1499-55-4)
• EPA Substance Registry System: L-Glutamic acid 5-methyl ester(1499-55-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 1499-55-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-Glutamic acid 5-methyl ester is used as a therapeutic agent for the treatment of patients with liver disease accompanied by encephalopathy (hepatic coma). It aids in managing the neurological complications associated with liver dysfunction.
Used in Neurotransmission:
L-Glutamic acid 5-methyl ester serves as a neurotransmitter for cone photoreceptors in the human brain, playing a vital role in the proper functioning of the central nervous system and maintaining overall brain health.
Used in Research and Development:
As a protected form of L-Glutamic acid, L-Glutamic acid 5-methyl ester is utilized in research and development for the synthesis of various pharmaceutical compounds and the study of its potential applications in neuroscience and neurodegenerative disorders.

InChI:InChI=1/C6H11NO4/c1-11-6(10)4(7)2-3-5(8)9/h4H,2-3,7H2,1H3,(H,8,9)

Upstream product

• 56-86-0 L-glutamic acid 
• 67-56-1 methanol 
• 138-15-8 l-glutamic acid hydrochloride 
• 1093125-21-3 C₂₉H₂₇NO₉ 
• 1293992-26-3 BrH*C₂₁H₂₁NO₇ 
• 75-36-5 acetyl chloride 
• 292638-85-8 acrylic acid methyl ester 
• 113890-30-5 2-((E)-((1S,2S,5S)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylidene)amino) acetate 
• 6525-53-7 L-glutamic acid dimethyl ester 
• 4124-76-9 N-(benzyloxycarbonyl)-L-glutamic acid anhydride 
• 3343-28-0 N-phthaloylglutamic acid anhydride 
• 617-65-2 Glutamic acid 
• 138036-14-3 2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-5-methoxy-5-oxopentanoic acid 

Downstream Products

• 1820-73-1 glutamic acid γ-hydrazide 
• 4652-65-7 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester 
• 79640-72-5 L-glutamic acid 1-tert-butyl ester 5-methyl ester 
• 5563-61-1 N-(N-Benzyloxycarbonyl-5-O-methyl-L-glutamyl)-L-glutaminsaeure-5-methylester 
• 3081-62-7 N-(γ-glutamyl)methylamine 
• 79974-19-9 N-<4-(methylamino)benzoyl>-L-glutamic acid γ-methyl ester 
• 53464-60-1 L-methyl folate (γ) 
• 113408-47-2 N-Trityl-L-glutaminsaeure-γ-methylester * Diethylamin 
• 149-87-1 Pyroglutamic acid 
• 6525-53-7 L-glutamic acid dimethyl ester 
• 97142-23-9 Z-L-glutamic acid γ-methyl ester DCHA salt 
• 6094-36-6 N-benzoyl-L-glutamic acid 

Relevant articles and documents

Asymmetric Synthesis of (+)-Phosphinothricin and Related Compounds by the Michael Addition of Glycine Schiff Bases to Vinyl Compounds

(S)-(+)-Phosphinothricin was prepared in good optical yield by th Michael addition of chiral glycine Schiff base derived from (S)-2-hydroxy-3-pinanone to vinyl phosphorus compound. (R)-(-)-Phosphinothricin, an enantiomeric isomer, can also be prepared from the same chiral glycine Schiff base by choosing suitable reaction temperature.

New access to the synthetic building block L-aspartic acid β-semialdehyde via Grignard reaction

A new, efficient, and inexpensive synthesis of protected L-aspartic acid β-semialdehyde has been developed starting from L-glutamic acid via a substituted L-allylglycine derivative as intermediate. The key step of the reaction sequence was a strongly solvent-dependent Grignard reaction of an L-glutamic acid semiester. The desired regioselective addition to the C-5 ester group was achieved in 1,2-dimethoxyethane while reactions in diethyl ether gave products resulting from additional attack at the carboxylic acid functionality.

Discovery of CRBN E3 Ligase Modulator CC-92480 for the Treatment of Relapsed and Refractory Multiple Myeloma

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ANTIPROLIFERATIVE COMPOUNDS AND METHODS OF USE THEREOF

Provided herein is 4-(4-(4-(((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)oxy)methyl)benzyl)piperazin-1-yl)-3-fluorobenzonitrile, or an enantiomer, a mixture of enantiomers, a tautomer, or a pharmaceutically acceptable salt thereof, and methods for treating, preventing or managing multiple myeloma using such compounds. Also provided are pharmaceutical compositions comprising the compounds, and methods of use of the compositions.

ANTIPROLIFERATIVE COMPOUNDS AND BISPECIFIC ANTIBODY AGAINST BCMA AND CD3 FOR COMBINED USE

Provided herein is are methods of using 4-(4-(4-(((2-(2,6-dioxopiperidin-3-yl)-l- oxoisoindolin-4-yl)oxy)methyl)benzyl)piperazin-l-yl)-3-fluorobenzonitrile, or an enantiomer, a mixture of enantiomers, a tautomer, or a pharmaceutically acceptable salt thereof and a bispecific antibody specifically binding to human B cell maturation antigen (BCMA) and to human CD3e (CD3) provided herein, in treating, preventing or managing multiple myeloma.

METHODS FOR TREATING MULTIPLE MYELOMA AND THE USE OF COMPANION BIOMARKERS FOR 4-(4-(4-(((2-(2,6-DIOXOPIPERIDIN-3-YL)-1-OXOISOINDOLIN-4-YL)OXY)METHYL)BENZYL)PIPERAZIN-1-YL)-3-FLUOROBENZONITRILE

A method of identifying a subject having cancer who is likely to be responsive to a treatment compound, comprising administering the treatment compound to the subject having the cancer; obtaining a sample from the subject; determining the level of a biomarker in the sample from the subject; and diagnosing the subject as being likely to be responsive to the treatment compound if the level of the biomarker in the sample of the subject changes as compared to a reference level of the biomarker; wherein the treatment compound is Compound 1, Compound 2, or Compound 3.

Tetrabutylammonium Fluoride as a Mild and Versatile Reagent for Cleaving Boroxazolidones to Their Corresponding Free α-Amino Acids

Protection of α-amino acids with 9-borabicyclo[3.3.1]nonane (9-BBN) to give their corresponding boroxazolidones is highly attractive, as it concurrently masks both the amino and the carboxylic acid functionalities. However, the harsh methods required for deprotection of these boroxazolidones have limited their use. Herein, we report that tetrabutylammonium fluoride serves as a mild and versatile reagent that can be used to cleave boroxazolidones to their corresponding free α-amino acids. The reaction conditions were explored, including the use of various nucleophilic fluoride sources, solvents, and reaction temperatures. Nucleophilic fluoride sources comprising an ammonium cation proved superior to other countercations. The scope of the reaction was extended to the cleavage of B,B-diphenyl- and B,B-diethyl boroxazolidone complexes. Furthermore, a wide range of α-amino acid side-chain functionalities were shown to be compatible, including acids, esters, amides, thiols, thioethers, alkynes, phenols, basic heterocycles, and important biorelevant molecules such as glutathione, (S)-adenosyl-l-homocysteine, and l-biocytin.

LYSINE ISOTOPOLOGUES, COMPOSITIONS COMPRISING THE SAME AND METHODS OF SYNTHESIS

This invention relates to lysine isotopologues of Formulas I and 1-A, as described herein, and processes for synthesizing the same and derivatives and intermediates involved therein. In one aspect, described herein is a chemical compound comprising an isotopically labeled analog, i.e., an isotopologue of a standard or naturally occurring lysine. The lysine isotopologue is synthetically formed to have stable isotopes of elements incorporated at selected positions. As such, the lysine isotopologue has a molecular mass different from the mass of a standard or naturally occurring lysine.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE a-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL] ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active α-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active α,α-disubstituted α-amino acid, and to provide an intermediate useful for the above production methods of an optically active α-amino acid and an optically active α,α-disubstituted α-amino acid. The present invention provides a production method of an optically active α-amino acid or a salt thereof, the production method comprising introducing a substituent into the α carbon in the α-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure α-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active ±-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ±,±-disubstituted ±-amino acid, and to provide an intermediate useful for the above production methods of an optically active ±-amino acid and an optically active ±,±-disubstituted ±-amino acid. The present invention provides a production method of an optically active ±-amino acid or a salt thereof, the production method comprising introducing a substituent into the ± carbon in the ±-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure ±-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.