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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

Beilstein:

1724348

MDL number:

MFCD00002636

UNSPSC Code:

12352209

PubChem Substance ID:

24278234

NACRES:

NA.32

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)

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)

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