L-Glutamic acid 5-methyl ester Chemical Properties

Melting point:

182 °C (dec.) (lit.)

alpha 

13 º (c=1, H2O 24 ºC)

Boiling point:

287.44°C (rough estimate)

Density 

1.3482 (rough estimate)

refractive index 

29 ° (C=2, 6mol/L HCl)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

Water Solubility 

Soluble in water

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

2.18±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

optical activity

[α]20/D +29°, c = 2 in 6 M HCl

BRN 

1725252

InChI

InChI=1S/C6H11NO4/c1-11-5(8)3-2-4(7)6(9)10/h4H,2-3,7H2,1H3,(H,9,10)/t4-/m0/s1

InChIKey

ZGEYCCHDTIDZAE-BYPYZUCNSA-N

SMILES

C(O)(=O)[C@H](CCC(OC)=O)N

CAS DataBase Reference

1499-55-4(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29224999

MSDS

• Language:English Provider:L-Glutamic acid gamma-methyl ester
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

L-Glutamic acid 5-methyl ester Usage And Synthesis

Chemical Properties

white amorphous powder

Uses

L-Glutamic acid 5-methyl ester is a protected form of L-Glutamic acid (G596960). L-Glutamic acid is a nonessential amino acid that is important to the mammalian central nervous system. L-Glutamic acid is also a neurotransmitter for cone photoreceptors in the human brain and is used as a treatment for patients who have liver disease accompanied by encephalopathy (a condition termed ‘hepatic coma’).

Definition

ChEBI: L-glutamic acid 5-methyl ester is a glutamic acid 5-methyl ester having L-configuration. It is a L-glutamic acid derivative, a non-proteinogenic L-alpha-amino acid and a glutamic acid 5-methyl ester.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

L-glutamic acid (22.1 g, 0.15 mol) was suspended in methanol (450 mL) at room temperature and under nitrogen protection. Subsequently, trimethylsilyl chloride (TMSCl, 35.9 g, 0.33 mol) was slowly added dropwise over a period of 5 min, at the end of which most of the solid was observed to be dissolved. Stirring of the reaction mixture was continued for 5 min and the progress of the reaction was monitored by thin layer chromatography (TLC, Spreader: 15% ammonia in methanol solution, Color Developer: ninhydrin) to confirm that only traces of the feedstock were present and that no bis-methyl esterified product was generated. After stirring again for 5 minutes, the reaction mixture was concentrated using a rotary evaporator and subsequently dried in a vacuum oven at 40 °C to give pure L-glutamic acid-5-methyl ester as a white solid. Yield: 30.0 g (100% yield). The structure of the product was confirmed by 1H NMR (300 MHz, CD3OD, ppm) δ 2.2 (2H, m), 2.6 (2H, m), 3.7 (3H, s), 4.1 (1H, t) and 13C NMR (75 MHz, CD3OD, ppm) δ 26.6, 30.4, 52.5, 53.2, 171.4, 174.3.

References

[1] Patent: US2016/16890, 2016, A1. Location in patent: Paragraph 0163
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 13, p. 3793 - 3797
[3] Tetrahedron Letters, 2010, vol. 51, # 9, p. 1333 - 1335
[4] Synthesis, 1987, # 7, p. 635 - 637
[5] Organic Process Research and Development, 2004, vol. 8, # 1, p. 72 - 85

L-Glutamic acid 5-methyl ester (1499-55-4)Related Product Information

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