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Key Documents

C7505

Sigma-Aldrich

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
Beilstein:
2505200
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26

product name

L-Cystathionine, ≥98% (TLC)

Assay

≥98% (TLC)

form

powder

technique(s)

UHPLC: suitable

color

white

mp

>300 °C

storage temp.

−20°C

SMILES string

N[C@@H](CCSC[C@H](N)C(O)=O)C(O)=O

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

InChI key

ILRYLPWNYFXEMH-WHFBIAKZSA-N

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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 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

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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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)
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
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
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)
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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