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A7275 Sigma-Aldrich

L-2-Aminoadipic acid

≥98% (TLC)

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

  • CAS Number 1118-90-7

  • Linear Formula HO2C(CH2)3CH(NH2)CO2H

  • Molecular Weight 161.16

  •  Beilstein/REAXYS Number 1724348

  •  MDL number MFCD00002636

  •  PubChem Substance ID 24278234

  •  NACRES NA.32

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Properties

Related Categories Cell Biology, Cell Signaling and Neuroscience, Enzyme Inhibitors, Glutamine Synthetase, Humulus lupulus (Hops),
Quality Level   200
assay   ≥98% (TLC)
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.

Packaging

1, 5 g in poly bottle

100, 250 mg in poly bottle

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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