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A8381

Sigma-Aldrich

L-Asparagine monohydrate

≥99% (TLC)

Synonym(s):

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

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About This Item

Linear Formula:
NH2COCH2CH(NH2)COOH · H2O
CAS Number:
5794-13-8
Molecular Weight:
150.13
Beilstein/REAXYS Number:
1723527
EC Number:
200-735-9
MDL number:
MFCD00151038
UNSPSC Code:
12352209
PubChem Substance ID:
24891338

biological source

synthetic

Quality Level

200

assay

≥99% (TLC)

form

powder

color

white to off-white

mp

233-235 °C (lit.)

application(s)

cell analysis
peptide synthesis

SMILES string

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

InChI

1S/C4H8N2O3.H2O/c5-2(4(8)9)1-3(6)7;/h2H,1,5H2,(H2,6,7)(H,8,9);1H2/t2-;/m0./s1

InChI key

RBMGJIZCEWRQES-DKWTVANSSA-N

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General description

Asparagine biosynthesis is catalyzed by glutamine-dependent asparagine synthetase in mammalian tissues. Elevated levels of free asparagine is observed in plants facing stress in the form of drought or high salt. It is also present in senescing leaves and germinating seeds.

Application

L-Asparagine monohydrate has been used:
  • as a component of Sauton′s and chelated Sauton′s media for mycobacterial growth
  • to test its effect in the induction of Ca2+ flux in rice roots using aequorin luminescence imaging
  • as a component of fermentation medium for the Blakeslea trispora spores

Biochem/physiol Actions

Asparagine has high nitrogen to carbon ratio and is a key regulator for nitrogen storage and transport. Its thermal degradation in the presence of sugars leads to the acrylamide formation in foods. Asparagine serves as an amino acid exchange factor and is essential for amino acid homeostasis. It favors cancer cell proliferation.
L-Asparagine, a proteinogenic amino acid, is used in biomanufacturing cell culture systems for the production of therapeutic recombinant proteins and monoclonal antibodies and in cell culture based research.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Construction of a network describing asparagine metabolism in plants and its application to the identification of genes affecting asparagine metabolism in wheat under drought and nutritional stress
Curtis TY, et al.
Food and energy security, 7(1), e00126-e00126 (2018)
Oxidative stress response and morphological changes of Blakeslea trispora induced by butylated hydroxytoluene during carotene production
Nanou K and Roukas T
Applied Biochemistry and Biotechnology, 160(8), 2415-2423 (2010)
Analysis of Mycobacterial Protein Secretion
Mehra A and Philips JA
Bio-protocol, 4(12), 11457-11457 (2014)
Asparagine in plants
Lea PJ, et al.
The Annals of applied biology, 150(1), 1-26 (2007)
Heterologous expression and functional analysis of rice GLUTAMATE RECEPTOR-LIKE family indicates its role in glutamate triggered calcium flux in rice roots
Ni J, et al.
Rice (New York, N.Y.), 9(1), 9-9 (2016)
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