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Merck
CN

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:
1118-90-7
Molecular Weight:
161.16
Beilstein:
1724348
MDL number:
MFCD00002636
UNSPSC Code:
12352209
PubChem Substance ID:
24278234
NACRES:
NA.32

Key Documents

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Product Name

L-2-Aminoadipic acid, ≥98% (TLC)

Quality Level

200

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)

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM7234
BCCL2753
BCCK3761
BCCH7080
BCCG2098

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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)
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
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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