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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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Properties

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)

Description

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.

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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)

Craigslist versus print newspaper advertising for recruiting research participants for alcohol studies: Cost and participant characteristics.

Christopher J Gioia et al.

Addictive behaviors, 54, 24-32 (2015-12-18)

Technology has transformed our lifestyles in dramatic and significant ways, including new and less expensive options for recruiting study participants. This study examines cost and participant differences between two recruitment sources, Craigslist (CL), and print newspapers (PNs). This paper also

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Global Trade Item Number

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