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A7275

L-2-Aminoadipic acid

Name: <SC>L</SC>-2-Aminoadipic acid
Brand: SIGMA

≥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

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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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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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)

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)

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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Global Trade Item Number

SKU	GTIN
A7275-250MG	04061833383971
A7275-1G	04061826731703
A7275-100MG	04061833383964
A7275-5G	04061833489598

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