A7275
L-2-Aminoadipic acid
≥98% (TLC), powder, glutamine synthetase inhibitor
Synonym(s):
(S)-2-Aminohexanedioic acid, L-Homoglutamic acid, Aad
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About This Item
Linear Formula:
HO2C(CH2)3CH(NH2)CO2H
CAS Number:
Molecular Weight:
161.16
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352209
MDL number:
Beilstein/REAXYS Number:
1724348
Product Name
L-2-Aminoadipic acid, ≥98% (TLC)
Quality Level
assay
≥98% (TLC)
form
powder
mp
203-205 °C (dec.) (lit.)
SMILES string
N[C@@H](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)/t4-/m0/s1
InChI key
OYIFNHCXNCRBQI-BYPYZUCNSA-N
Gene Information
human ... GLUL(2752), LGSN(51557)
rat ... Grm1(24414), Grm2(24415), Grm4(24417), Grm5(24418), Grm6(24419)
General description
L-2-Aminoadipic acid/α-aminoadipate is a gliotoxin and is a structural analog of glutamine. It is generated by the catabolism of lysine saccharopine (SAC)/pipecolic acid (PIP) pathways.
Application
L-2-Aminoadipic acid has been used as a gliotoxin specific for astrocytes in rat. It has also been as an internal standard in the amino acid analysis from fermented food sample.
Biochem/physiol Actions
L-2-Aminoadipic acid inhibits glutamine synthetase and γ-glutamylcysteine synthetase. It modulates glucose metabolism and is present in higher levels in diabetic patients. L-2-Aminoadipic acid plays a key role in suppressing autophagy in C2C12 myotubes.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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2-Aminoadipic acid is a biomarker for diabetes risk
Wang TJ, et al.
The Journal of Clinical Investigation, 123(10), 4309-4317 (2013)
GABA ergic inhibition through synergistic astrocytic neuronal interaction transiently decreases vasopressin neuronal activity during hypoosmotic challenge
Wang YF, et al.
The European Journal of Neuroscience, 37(8), 1260-1269 (2013)
Astrocytes Protect Neurons in the Hippocampal CA3 Against Ischemia by Suppressing the Intracellular Ca2+ Overload
Sun C, et al.
Frontiers in Cellular Neuroscience, 12, 2168-2175 (2018)