N-CARBAMYL-L-GLUTAMIC ACID Chemical Properties

Melting point:

174°

Boiling point:

438.1±45.0 °C(Predicted)

Density 

1.499±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

3.71±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C6H10N2O5/c7-6(13)8-3(5(11)12)1-2-4(9)10/h3H,1-2H2,(H,9,10)(H,11,12)(H3,7,8,13)/t3-/m0/s1

InChIKey

LCQLHJZYVOQKHU-VKHMYHEASA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37

WGK Germany 

3

RTECS 

LZ9870000

HS Code 

2924190002

MSDS

• Language:English Provider:SigmaAldrich

N-CARBAMYL-L-GLUTAMIC ACID Usage And Synthesis

Uses

carbamylphosphate synthetase activator

Uses

N-Carbamyl-L-glutamic Acid has been shown to have protective effects against ammonia intoxication and is used in the treatment of acute hyperammonemia.

Definition

ChEBI: A urea that is the N-carbamoyl derivative of L-glutamic acid. An orphan drug used to treat a deficiency in the enzyme N-acetylglutamate synthase, which leads to acute hyperammonaemia.

Biological Activity

N-Carbamyl-L-glutamic acid (carglumic acid) is use to study its potential as a replacement therapy for N-acetylglutamate synthetase (NAGS) deficiency and to tre at hyperammonemia.

Synthesis

The general procedure for the synthesis of N-carbamoyl-L-glutamic acid from potassium cyanate and L-glutamic acid was as follows: 4 mmol of L-glutamic acid was dissolved in 20 mL of water and the solution was acidified using concentrated hydrochloric acid (37 μL, v/v). Subsequently, 12 mmol of potassium thiocyanate (KOCN) was added to the acidified solution. The reaction mixture was heated to 333 K under continuous stirring and maintained at this temperature for 4 hours. Upon completion of the reaction, the solution was cooled to room temperature and transferred to a glass vial sealed with a closure film, which was perforated to promote solvent evaporation until a white solid was observed to precipitate. Crystals of (I) suitable for X-ray single crystal diffraction analysis were grown at room temperature by slow evaporation of the ethanol solution (see Scheme 1). The yield of this synthetic method was 62% and the melting points of the resulting products ranged from 170°C to 171°C. This experimental procedure is an improvement and optimization of a previously reported method.

in vivo

References

[1] Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 225 - 232
[2] Pharmaceutical Chemistry Journal, 1978, vol. 12, # 5, p. 601 - 606
[3] Khimiko-Farmatsevticheskii Zhurnal, 1978, vol. 12, # 5, p. 53 - 59

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