sigmaL-天冬酰胺

L-Asparagine monohydrate

Product Number A 8381

Store at Room Temperature

Product Description

Molecular Formula: C4H8N2O3 • H2O

Molecular Weight: 150.1

CAS Number: 5794-13-8

pKa: 2.14 （-COOH）, 8.72 （-NH2）1

pI: 5.431

Specific Rotation: +32.6°

（10 mg/ml, 0.1 M HCl, 20 °C）

Melting Point: 234-235 °C2

Synonyms: （S）-2-aminosuccinic acid 4-amide,

L-aspartic acid 4-amide, α-aminoauccinamic acid,

aspartic acid β-amide2

The amino acid L-asparagine is a structural analog of

L-aspartic acid, where the side chain of the carboxylic

acid moiety is amidated, to give a terminal amine

group. This renders L-asparagine neutral at

physiological pH. The amide group of asparagine is

derived from glutamate, in the reaction of aspartate

and glutamine in the presence of ATP to yield

asparagine and glutamate.3 In vivo, asparagine is

hydrolyzed to aspartate and NH4

+ by asparaginase.4

Asparagine is also an important amino acid in

glycopeptide bonds, via N-glycosyl linkages to the

sugar rings.3

L-Asparagine is used in cell culture media and is a

component of MEM non-essential amino acids solution

（Product No. M 7145）. L-Asparagine has been shown

to enhance ornithine decarboxylase activity in cultured

human colon adenocarcinoma Caco-2 cells and in

cultured IEC-6 intestinal epithelial cells.5,6 Spore

germination in Bacillus subtilis has been increased in

the presence of L-asparagine.7

An isoxazoline RGD mimic plaet GPIIb/IIIa

antagonist has been prepared by chiral synthesis with

L-asparagine as a starting material.8 L-Asparagine

has been utilized in the synthesis of 4-azalysine

building blocks for application to combinatorial

chemistry.9

Precautions and Disclaimer

For Laboratory Use Only. Not for drug, household or

other uses.

Preparation Instructions

This product is soluble in water （50 mg/ml）, with heat

as needed, yielding a clear, colorless solution.

References

1. Molecular Biology Lab, Brown, T. A., ed., BIOS

Scientific Publishers （Oxford, UK: 1991）, p. 29.

2. The Merck Index, 12th ed., Entry# 872.

3. Textbook of Biochemistry with Clinical

Correlations, 5th ed., Devlin, T. M., ed., Wiley-Liss

（New York, NY: 2002）, pp. 97, 680-681, 785-786.

4. Biochemistry, 3rd ed., Stryer, L., W. H. Freeman

（New York, NY: 1988）, pp. 18, 504.

5. Chabanon, H., et al., Increased translation

efficiency and antizyme-dependent stabilization of

ornithine decarboxylase in amino acidsupplemented

human colon adenocarcinoma

cells, Caco-2. Biochem. J., 348（Pt 2）, 401-408

（2000）.

6. Ray, R. M., et al., Interaction of asparagine and

EGF in the regulation of ornithine decarboxylase in

IEC-6 cells. Am. J. Physiol., 276（3 Pt 1）, G773-

780.

7. Cabrera-Martinez, R. M., et al., Effects of

overexpression of nutrient receptors on

germination of spores of Bacillus subtilis. J.

Bacteriol., 185（8）, 2457-2464 （2003）.

8. Zhang L. H., et al., The Enantiospecific synthesis

of an isoxazoline. A RGD mimic plaet GPIIb/IIIa

antagonist. J. Org. Chem., 62（8）, 2466-2470

（1997）.

9. Chhabra, S. R., et al., Homochiral 4-azalysine

building blocks: syntheses and applications in

solid-phase chemistry. J. Org. Chem., 67（12）,

4017-4029 （2002）.

GCY/RXR 8/03

Sigma brand

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