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A7400

Sigma-Aldrich

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:
7620-28-2
Molecular Weight:
161.16
Beilstein/REAXYS Number:
1724347
MDL number:
MFCD00063118
UNSPSC Code:
12352106
PubChem Substance ID:
24891125
NACRES:
NA.32

form

powder

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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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