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

hazcat

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

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...
The toxic effect of sodium glutamate and DL-$\alpha$-aminoadipic acid on rat retina: Changes in high affinity uptake of putative transmitters
Karlsen RL, et al.
Journal of Neurochemistry, 31(4), 1055-1061 (1978)
Gliotoxic effects of $\alpha$-aminoadipic acid on monolayer cultures of dissociated postnatal mouse cerebellum
Huck S, et al.
Neuroscience, 12(3), 783-791 (1984)
Gliotoxin-induced swelling of astrocytes hinders diffusion in brain extracellular space via formation of dead-space microdomains
Sherpa AD, et al.
Glia, 62(7), 1053-1065 (2014)

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