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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
Assay:
≥98% (TLC)
Form:
powder
Quality level:
200

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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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)
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
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)
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