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A7400

Sigma-Aldrich

D-2-Aminoadipic acid

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Synonym(s):
(R)-2-Aminohexanedioic acid, D-Homoglutamic acid
Linear Formula:
HO2C(CH2)3CH(NH2)CO2H
CAS Number:
7620-28-2
Molecular Weight:
161.16
Beilstein:
1724347
MDL number:
MFCD00063118
PubChem Substance ID:
24891125
NACRES:
NA.32

form

powder

Quality Level

200

mp

208-210 °C (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-/m1/s1

InChI key

OYIFNHCXNCRBQI-SCSAIBSYSA-N

Gene Information

rat ... Grin2a(24409) , Grm1(24414) , Grm2(24415) , Grm6(24419)

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Application

D-2-Aminoadipic acid has been used as an inhibitor of glutamine synthetase in spontaneously immortalized human cell line MIO-M1.

Biochem/physiol Actions

D-2-Aminoadipic acid is a glutamate analog. It acts as an inhibitor of glutamate synthetase. D-2-Aminoadipic acid exhibits gliotoxicity towards mitotic astrocytes.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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D R Brown et al.
Journal of neurocytology, 27(2), 109-118 (1998-06-03)
The mechanism of action of the glutamate analogue alpha-aminoadipic (AAA) acid was investigated in terms of its toxicity to cultured astrocytes. AAA was more toxic to type 1 astrocytes than type 2 astrocytes. Also the higher toxicity of the L-isomer
T P Hicks et al.
Neuroscience research, 24(2), 139-150 (1996-01-01)
Many studies on long-term potentiation (LTP) in hippocampal region CA1 focus on receptor-mediated events that are often presumed to be linked to postsynaptic processes. Whereas it is now well-known that LTP consists of multiple components involving increases in postsynaptic responsiveness
Wang-Yang Xu et al.
The Journal of endocrinology, 243(2), 111-123 (2019-08-28)
Obesity and type 2 diabetes (T2D) are both complicated endocrine disorders resulting from an interaction between multiple predisposing genes and environmental triggers, while diet and exercise have key influence on metabolic disorders. Previous reports demonstrated that 2-aminoadipic acid (2-AAA), an
Yang Guo et al.
Experimental eye research, 210, 108703-108703 (2021-07-20)
Diabetic retinopathy (DR) is a vision-loss complication caused by diabetes with high prevalence. During DR, the retinal microvascular injury and neurodegeneration derived from chronic hyperglycemia have attracted global attention to retinal Müller cells (RMCs), the major macroglia in the retina
S Servotte et al.
Protoplasma, 229(2-4), 215-220 (2006-12-21)
Small GTP-binding proteins of the Rho family (RhoA, Cdc42, Rac1) regulate the organisation and the turnover of the cell's cytoskeleton and adhesion structures. A significant function of these cellular structures is to translate and counterbalance forces applied to, or generated
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