A7400
D-2-Aminoadipic acid
Synonym(s):
(R)-2-Aminohexanedioic acid, D-Homoglutamic acid
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All Photos(2)
About This Item
Linear Formula:
HO2C(CH2)3CH(NH2)CO2H
CAS Number:
Molecular Weight:
161.16
Beilstein:
1724347
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.32
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form
powder
Quality Level
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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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
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
G J McBean
British journal of pharmacology, 113(2), 536-540 (1994-10-01)
1. The effect of the gliotoxic analogue of glutamate, alpha aminoadipate, on the high affinity transport of D-[3H]-aspartate into a crude striatal P2 preparation, and on the activity of two enzymes of which glutamate is the substrate has been examined.
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