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A0637

Sigma-Aldrich

DL-2-Aminoadipic acid

≥99%

Synonym(s):
DL-α-Aminoadipic acid
Linear Formula:
HO2C(CH2)3CH(NH2)CO2H
CAS Number:
Molecular Weight:
161.16
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥99%

mp

196-198 °C (lit.)

storage temp.

2-8°C

SMILES string

NC(CCCC(O)=O)C(O)=O

InChI

1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)

InChI key

OYIFNHCXNCRBQI-UHFFFAOYSA-N

Gene Information

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Application

DL-2-Aminoadipic acid (AAA) has been used as an astrotoxin to kill astrocytes that prevent efficient integration of transplanted cells into the retina. It has also been used as a gliotoxin to study the effect of astrocytic swelling on the tortuosity.

Biochem/physiol Actions

DL-2-Aminoadipic acid (AAA) is a six-carbon homolog of glutamate and a gliotoxic compound. It is generally used to considerably reduce the number of astroglia in cerebellar cultures that acts as a model to study the mechanisms of a-aminoadipic acid induced glial toxicity.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A0637.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

pictograms

Exclamation mark

signalword

Warning

hcodes

pcodes

Hazard Classifications

Skin Sens. 1

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

H Bräuner-Osborne et al.
Journal of medicinal chemistry, 39(16), 3188-3194 (1996-08-02)
The homologous series of acidic amino acids, ranging from aspartic acid (1) to 2-aminosuberic acid (5), and the corresponding series of 3-isoxazolol bioisosteres of these amino acids, ranging from (RS)-2-amino-2-(3-hydroxy-5-methylisoxazol-4-yl)acetic acid (AMAA, 6) to (RS)-2-amino-6-(3-hydroxy-5-methylisoxazol-4-yl)hexanoic acid (10), were tested as...
Saadet Mercimek-Mahmutoglu et al.
Pediatrics, 129(5), e1368-e1372 (2012-04-25)
Pyridoxine-dependent epilepsy (PDE) was first described in 1954. The ALDH7A1 gene mutations resulting in α-aminoadipic semialdehyde dehydrogenase deficiency as a cause of PDE was identified only in 2005. Neonatal epileptic encephalopathy is the presenting feature in >50% of patients with...
Bhagyalaxmi S Ganesh et al.
PloS one, 6(3), e18305-e18305 (2011-04-13)
Reactive gliosis is a hallmark of many retinal neurodegenerative conditions, including glaucoma. Although a majority of studies to date have concentrated on reactive gliosis in the optic nerve head, very few studies have been initiated to investigate the role of...
H Q Wu et al.
European journal of pharmacology, 281(1), 55-61 (1995-07-25)
L-alpha-Aminoadipic acid is a lysine metabolite with neuroexcitatory properties, and has previously been shown to inhibit the production of the broad spectrum excitatory amino acid receptor antagonist kynurenic acid in brain tissue slices. The effects of L-alpha-aminoadipic acid on the...
Huadong Ni et al.
Journal of neuroinflammation, 16(1), 1-1 (2019-01-05)
Despite accumulating evidence on the role of glial cells and their associated chemicals in mechanisms of pain, few studies have addressed the potential role of chemokines in the descending facilitation of chronic pain. We aimed to study the hypothesis that...

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