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MilliporeSigma

55398

Supelco

L-2-Aminoadipic acid

analytical standard

Sinónimos:

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

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About This Item

Fórmula lineal:
HO2C(CH2)3CH(NH2)CO2H
Número de CAS:
Peso molecular:
161.16
Beilstein/REAXYS Number:
1724348
MDL number:
UNSPSC Code:
41116107

grade

analytical standard

assay

≥98% (TLC)

optical activity

[α]25/D 24±1°, c = 2 in 5 M HCl

shelf life

limited shelf life, expiry date on the label

mp

203-205 °C (dec.) (lit.)

application(s)

clinical testing

format

neat

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

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General description

L-2-Aminoadipic acid is the six-carbon homolog of glutamate and a metabolite of L-lysine.

Application

L-2-Aminoadipic acid may be used as an analytical standard in the following:
  • For the quantification of 2-aminoadipic acid in acid hydrolysates of processed skin samples using gas chromatography coupled to mass spectrometry (GC-MS).
  • To investigate its effect on proteolysis and protein synthesis in C2C12 myotubes.

It may be used as an internal standard for the determination of free amino acids and ammonium ion contents in Crocus sativus L. from different geographical origins using high-performance liquid chromatography with diode array detection (HPLC-DAD).

Recommended products

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Determination of free amino acids and ammonium ion in saffron (Crocus sativus L.) from different geographical origins
Campo dPC, et al.
Food Chemistry, 114(4), 1542-1548 (2009)
Maho Shibata et al.
Investigative ophthalmology & visual science, 53(7), 3726-3732 (2012-05-17)
To investigate the involvement of glial cells in the autoregulation of optic nerve head (ONH) blood flow in response to elevated intraocular pressure (IOP). Rabbit eyes were treated with an intravitreal injection of l-2-aminoadipic acid (LAA), a gliotoxic compound. Twenty-four
David R Sell et al.
The Biochemical journal, 404(2), 269-277 (2007-02-23)
We hypothesized that the epsilon-amino group of lysine residues in longlived proteins oxidatively deaminates with age forming the carbonyl compound, allysine (alpha-aminoadipic acid-delta-semialdehyde), which can further oxidize into 2-aminoadipic acid. In the present study, we measured both products in insoluble
Regulatory effects of the L-lysine metabolites, L-2-aminoadipic acid and L-pipecolic acid, on protein turnover in C2C12 myotubes
Sato T, et al.
Bioscience, Biotechnology, and Biochemistry, 80(11), 2168-2175 (2016)

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