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About This Item
Empirical Formula (Hill Notation):
C7H14N2O4S
CAS Number:
Molecular Weight:
222.26
NACRES:
NA.26
PubChem Substance ID:
UNSPSC Code:
12352209
EC Number:
200-295-8
MDL number:
Beilstein/REAXYS Number:
2505200
Product Name
L-Cystathionine, ≥98% (TLC)
InChI key
ILRYLPWNYFXEMH-WHFBIAKZSA-N
InChI
1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1
SMILES string
N[C@@H](CCSC[C@H](N)C(O)=O)C(O)=O
assay
≥98% (TLC)
form
powder
technique(s)
UHPLC: suitable
color
white
mp
>300 °C
storage temp.
−20°C
Quality Level
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Application
L-Cystathionine has been used in ultra-performance liquid chromatography for the validation of cystathionine and the correlation of its abundance with vertebrate metamorphosis. It has also been used as an inhibitor of sinusoidal GSH (glutathione) carrier to signify that thiol redox state imbalance is associated with the modulation of autophagy in carcinoma cells.
Biochem/physiol Actions
L-Cystathionine is an intermediate in the biosynthesis of L-cysteine and methionine. It is used as a substrate to differentiate and analyze cystathionine γ-lyase(s). L-Cystathionine is an important non-protein amino acid and is associated with metabolic disorders. In recent studies, L-cystathionine is believed to be the precursor of cyclic imino acid cyclothionine. Cystathioninuria is characterized with imino acid cyclothionine excretion in the urine.
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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The transamination of L-cystathionine, L-cystine and related compounds by a bovine kidney transaminase.
Ricci G
European Journal of Biochemistry, 157(1), 57-63 (1986)
Synthesis and evaluation of L-cystathionine as a standard for amino acid analysis.
Amino Y
Bioscience, Biotechnology, and Biochemistry, 81(1), 95-101 (2017)
Cysteine and obesity: consistency of the evidence across epidemiologic, animal and cellular studies.
Amany K Elshorbagy et al.
Current opinion in clinical nutrition and metabolic care, 15(1), 49-57 (2011-11-24)
The concentrations of several plasma amino acids increase in obesity. Notably, plasma total concentrations of the sulphur amino acid cysteine (tCys) are linearly associated with fat mass in large population studies. Animal and cellular experiments support the concept that cysteine
Moemen S Hanafy et al.
Journal of plant physiology, 170(3), 338-345 (2013-01-05)
Methionine (Met) is a sulfur-containing amino acid that is essential in mammals and whose low abundance limits the nutritional value of grain legumes. Cystathionine γ-synthase (CGS) catalyzes the first committed step of Met biosynthesis, and the stability of its mRNA
G Ricci et al.
The Journal of biological chemistry, 258(17), 10511-10517 (1983-09-10)
L-Cystathionine is oxidized by snake venom L-amino acid oxidase at a rate about half that with L-leucine at pH 8.5. The appearance of an absorbance at 296 nm and quantitation of the products of oxidation in the presence of catalase
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