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MilliporeSigma

A7275

Sigma-Aldrich

L-2-Aminoadipic acid

≥98% (TLC), powder, glutamine synthetase inhibitor

Sinónimos:

(S)-2-Aminohexanedioic acid, L-Homoglutamic acid, Aad

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About This Item

Fórmula lineal:
HO2C(CH2)3CH(NH2)CO2H
Número de CAS:
Peso molecular:
161.16
Beilstein/REAXYS Number:
1724348
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.32

Nombre del producto

L-2-Aminoadipic acid, ≥98% (TLC)

Quality Level

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

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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Visite la Librería de documentos

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)
Regulatory effects of the L-lysine metabolites, L-2-aminoadipic acid and L-pipecolic acid, on protein turnover in C2C12 myotubes
Sato T, et al.
Bioscience, Biotechnology, and Biochemistry, 80(11), 2168-2175 (2016)
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
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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