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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
NACRES:
NA.32
PubChem Substance ID:
24278234
UNSPSC Code:
12352209
MDL number:
MFCD00002636
Beilstein/REAXYS Number:
1724348

Key Documents

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Product Name

L-2-Aminoadipic acid, ≥98% (TLC)

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

SMILES string

N[C@@H](CCCC(O)=O)C(O)=O

InChI key

OYIFNHCXNCRBQI-BYPYZUCNSA-N

assay

≥98% (TLC)

form

powder

mp

203-205 °C (dec.) (lit.)

Quality Level

200

Gene Information

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

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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.

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.

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCM7234
BCCL2753
BCCK3761
BCCH7080
BCCG2098

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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)
Fermentation of seeds of Teff (Eragrostis teff), grass-pea (Lathyrus sativus), and their mixtures: aspects of nutrition and food safety
Yigzaw Y, et al.
Journal of Agricultural and Food Chemistry, 52(5), 1163-1169 (2004)
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)
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)
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