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A7275

Sigma-Aldrich

L-2-Aminoadipic acid

≥98% (TLC)

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Synonym(s):
(S)-2-Aminohexanedioic acid, L-Homoglutamic acid, Aad
Linear Formula:
HO2C(CH2)3CH(NH2)CO2H
CAS Number:
Molecular Weight:
161.16
Beilstein/REAXYS Number:
1724348
MDL number:
PubChem Substance ID:
NACRES:
NA.32

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

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1 of 4

This Item
A0637A740011189
vibrant-m

A7275

L-2-Aminoadipic acid

-
vibrant-m

A0637

DL-2-Aminoadipic acid

-
vibrant-m

A7400

D-2-Aminoadipic acid

-
vibrant-m

11189

L-Aspartic acid

Premium Grade
form

powder

form

powder

form

powder

form

powder or crystals

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

mp

203-205 °C (dec.) (lit.)

mp

196-198 °C (lit.)

mp

208-210 °C (lit.)

mp

>300 °C (dec.) (lit.)

Gene Information

human ... GLUL(2752), LGSN(51557)
rat ... Grm1(24414), Grm2(24415), Grm4(24417), Grm5(24418), Grm6(24419)

Gene Information

rat ... Grin2b(24410)

Gene Information

rat ... Grin2a(24409), Grm1(24414), Grm2(24415), Grm6(24419)

Gene Information

human ... CA1(759), CA2(760)
rat ... Grin2a(24409)

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.

Storage Class

11 - Combustible Solids

wgk_germany

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)
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)
M E Alañón et al.
Food research international (Ottawa, Ont.), 101, 239-248 (2017-09-25)
With the aim of looking for a model of agroecological production, the use of by-products from pyro-bituminous shale as amendment, and its effect on wine amino acids and biogenic amines has been evaluated. Field trials aimed to compare the effect
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)
Inhibition of the glutamate transporter and glial enzymes in rat striatum by the gliotoxin, ocaminoadipate
McBean, Gethin J
British Journal of Pharmacology, 113(2), 536-540 (1994)

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