A7400
D-2-Aminoadipic acid
Synonym(s):
(R)-2-Aminohexanedioic acid, D-Homoglutamic acid
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About This Item
Linear Formula:
HO2C(CH2)3CH(NH2)CO2H
CAS Number:
Molecular Weight:
161.16
UNSPSC Code:
12352106
NACRES:
NA.32
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1724347
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
SMILES string
N[C@H](CCCC(O)=O)C(O)=O
InChI key
OYIFNHCXNCRBQI-SCSAIBSYSA-N
form
powder
mp
208-210 °C (lit.)
Quality Level
Gene Information
rat ... Grin2a(24409), Grm1(24414), Grm2(24415), Grm6(24419)
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Related Categories
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
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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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
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
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
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
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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