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Key Documents

A4159

Sigma-Aldrich

L-Asparagine

BioReagent, suitable for cell culture, suitable for insect cell culture

Synonym(s):

(S)-2-Aminosuccinic acid 4-amide, L-Aspartic acid 4-amide

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About This Item

Linear Formula:
H2NCOCH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
132.12
Beilstein:
1723527
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.75

product line

BioReagent

Assay

≥98% (HPLC)

form

powder

technique(s)

cell culture | insect: suitable
cell culture | mammalian: suitable

color

white

mp

235 °C (dec.) (lit.)

application(s)

agriculture

SMILES string

N[C@@H](CC(N)=O)C(O)=O

InChI

1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1

InChI key

DCXYFEDJOCDNAF-REOHCLBHSA-N

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Application

L-Asparagine is used in cell culture media and is a component of MEM non-essential amino acids solution. 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. Spore germination in Bacillus subtilis has been increased in the presence of L-asparagine.
An isoxazoline RGD mimic platelet GPIIb/IIIa antagonist has been prepared by chiral synthesis with L-asparagine as a starting material. L-Asparagine has been utilized in the synthesis of 4-azalysine building blocks for application to combinatorial chemistry.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The enantiospecific synthesis of an isoxazoline. A RGD mimic platelet GPIIb/IIIa antagonist.
Zhang L. H., et al.
The Journal of Organic Chemistry, 62, 2466-270 (1997)
Interaction of asparagine and EGF in the regulation of ornithine decarboxylase in IEC-6 cells
Ray, R. M., et al.
The American Journal of Physiology, 276 (3 Pt 1), G773-G780 null
Increased translation efficiency and antizyme-dependent stabilization of ornithine decarboxylase in amino acidsupplemented human colon adenocarcinoma cells, Caco-2.
Chabanon, H., et al.
The Biochemical Journal, 348 (Pt 2), 401-408 (2000)
Effects of overexpression of nutrient receptors on germination of spores of Bacillus subtilis
Cabrera-Martinez, R. M., et al.
Journal of Bacteriology, 185, 2457-264 (2003)
Homochiral 4-azalysine building blocks: syntheses and applications in solid-phase chemistry
Chhabra, S. R., et al.
The Journal of Organic Chemistry, 67, 4017-4029 (2002)

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