A7275

L-2-Aminoadipic acid

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

• Synonym(s): (S)-2-Aminohexanedioic acid, L-Homoglutamic acid, Aad
• Linear Formula: HO₂C(CH₂)₃CH(NH₂)CO₂H
• CAS Number: 1118-90-7
• Molecular Weight: 161.16
• Beilstein/REAXYS Number: 1724348
• MDL number: MFCD00002636
• UNSPSC Code: 12352209
• PubChem Substance ID: 24278234
• NACRES: NA.32

Properties

• product name: L-2-Aminoadipic acid, ≥98% (TLC)
• 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.

Safety Information

• 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)