C7505
L-Cystathionine
≥98% (TLC), suitable for UHPLC
Synonym(s):
(R)-S-(2-Amino-2-carboxyethyl)-L-homocysteine
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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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Synthesis and evaluation of L-cystathionine as a standard for amino acid analysis.
Amino Y
Bioscience, Biotechnology, and Biochemistry, 81(1), 95-101 (2017)
Cystathionine gamma-lyase of Streptomyces phaeochromogenes. The occurrence of cystathionine gamma-lyase in filamentous bacteria and its purification and characterization.
Nagasawa T
The Journal of Biological Chemistry, 259(16), 10393-10403 (1984)
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)
Amany K Elshorbagy et al.
Nutrition (Burbank, Los Angeles County, Calif.), 26(11-12), 1201-1204 (2010-01-19)
Dietary methionine restriction in Fischer-344 rats favorably influences visceral fat mass, insulin sensitivity, metabolic parameters, and longevity. However, little is known about the effects of methionine restriction on serum methionine and its downstream sulfur amino acids. We investigated the serum
Zoltan Dekan et al.
Journal of the American Chemical Society, 133(40), 15866-15869 (2011-09-09)
The two disulfide bonds of α-conotoxin ImI, a peptide antagonist of the α7 nicotinic acetylcholine receptor (nAChR), were systematically replaced with isosteric redox-stable cystathionine thioethers. Regioselective thioether formation was accomplished on solid support through substitution of a γ-chlorohomoalanine by an
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