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L-Cystathionine

Alias: Cystathionine, L- L-(+)-Cystathionine L-Cystathionine
Cat No.:V18189 Purity: ≥98%
L-Cystathionine is a non-protein and sulfur-containing amino acid associated with the metabolism of sulfur-containing amino acids.
L-Cystathionine
L-Cystathionine Chemical Structure CAS No.: 56-88-2
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
25mg
50mg
100mg
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Other Forms of L-Cystathionine:

  • DL-Cystathionine
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
L-Cystathionine is a non-protein and sulfur-containing amino acid associated with the metabolism of sulfur-containing amino acids. As a key nonprotein amino acid related to metabolic conditions, it protects against Homocysteine-induced mitochondria-dependent apoptosis of vascular endothelial cells (HUVECs) and plays an important role in cardiovascular protection.
L-Cystathionine is a non-protein, sulfur-containing amino acid that serves as a key intermediate in the transsulfuration pathway. It is formed from L-homocysteine and L-serine by cystathionine β-synthase (CBS, EC 4.2.1.22). It is then converted to L-cysteine and α-ketobutyrate by cystathionine γ-lyase (CGL, EC 4.4.1.1).
Biological Activity I Assay Protocols (From Reference)
Targets
L-Cystathionine is a substrate for cystathionine γ-lyase (CGL), an enzyme involved in the transsulfuration pathway. It is also a substrate for cystathionine β-synthase (CBS) in the reverse direction. It is a precursor for glutathione synthesis through cysteine. It plays a role in homocysteine metabolism.
ln Vitro
Manhattan was markedly increased by homocysteine in HUVEC, an effect that L-cystathionine residues dramatically attenuated. Furthermore, L-cystathionine mitochondria increases mitochondrial membrane potential, inhibits the opening of the mitochondrial permeability transition pore (MPTP), decreases the production of superoxide label, and expresses Bax while blocking its transport to mitochondria. It also prevents cytochrome c from leaking from mitochondria into the cytoplasm. , and fold the caspase-3 and caspase-9 activities [1]. L-cystathionine plays a significant role in auxiliary tissues and is a mediator in the L-cysteine transsulfurization route of L-methionine via L-homocysteine [2].
In vitro, L-cystathionine serves as the native substrate in assays of cystathionine γ-lyase activity. Relative enzyme activity with various substrates is: L-djenkolic acid > L-cystine > L-cysteine > L-methionine > L-serine. It is oxidized by snake venom L-amino acid oxidase at about half the rate of L-leucine at pH 8.5.
ln Vivo
In vivo, L-cystathionine is an endogenous metabolite found in humans, yeast, E. coli, and mice. It plays a critical role in sulfur amino acid metabolism and is involved in the biosynthesis of cysteine and glutathione. Abnormal cystathionine levels are associated with metabolic disorders.
Enzyme Assay
L-Cystathionine is used as a substrate in enzyme activity assays for cystathionine γ-lyase (CGL). The assay typically involves incubating L-cystathionine with CGL enzyme in appropriate buffer. The production of cysteine or α-ketobutyrate is measured spectrophotometrically using chromogenic reagents (e.g., DTNB for cysteine, or NADH-coupled assays for α-ketobutyrate).
Cell Assay
In vitro cell culture experiments use L-cystathionine as a substrate to study transsulfuration pathway activity. Cells are treated with L-cystathionine, and intracellular cysteine and glutathione levels are measured by HPLC or LC-MS/MS. Enzyme activity is assessed by measuring product formation from L-cystathionine in cell lysates.
Animal Protocol
In vivo studies measure L-cystathionine levels in biological samples (plasma, urine, tissues) as a biomarker of transsulfuration pathway activity. Animal models of metabolic disorders (e.g., CBS deficiency, homocystinuria) are used to study L-cystathionine metabolism. L-cystathionine may be administered orally or intraperitoneally.
ADME/Pharmacokinetics
L-Cystathionine is an endogenous metabolite that is absorbed and metabolized in the body. It is produced in the transsulfuration pathway and is rapidly converted to cysteine by cystathionine γ-lyase. Plasma levels are normally low but may be elevated in certain metabolic disorders such as cystathioninuria (CGL deficiency).
Toxicity/Toxicokinetics
L-Cystathionine is generally considered non-toxic as it is an endogenous metabolite. However, elevated levels of cystathionine (cystathioninuria) may indicate enzyme deficiency (cystathionine γ-lyase deficiency) but is generally considered a benign condition. High doses in experimental settings are well-tolerated.
References

[1]. L-Cystathionine Protects against Homocysteine-Induced Mitochondria-Dependent Apoptosis of Vascular Endothelial Cells. Oxid Med Cell Longev. 2019 Nov 25;2019:1253289.

[2]. Synthesis and evaluation of L-cystathionine as a standard for amino acid analysis. Biosci Biotechnol Biochem. 2017 Jan;81(1):95-101.

Additional Infomation
L-cystathionine is a modified amino acid produced by an enzymatic reaction of L-homocysteine and L-serine. It is found in humans, Saccharomyces cerevisiae, Escherichia coli, and mice, and is a zwitterion tautomer of L-cystathionine. L-cystathionine is a metabolite found or produced in Escherichia coli (K12 strain, MG1655 strain). It has been reported to exist in Equisetum hyemale, Daphnia frenulum, and other organisms with relevant data. Cystathionine is an amino acid derivative and an intermediate in cysteine biosynthesis. It is formed by the linkage of homocysteine and serine under the action of cystathionine β-synthetase. Sulfur-containing amino acids are intermediates in the conversion of methionine to cysteine.
L-Cystathionine is a naturally occurring amino acid that plays a central role in sulfur metabolism. It is an important intermediate in the biosynthesis of cysteine from methionine via the transsulfuration pathway. It is used as a research tool to study homocysteine metabolism, cysteine biosynthesis, and glutathione production.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C7H14N2O4S
Molecular Weight
222.25
Exact Mass
222.067
CAS #
56-88-2
Related CAS #
L-Cystathionine dihydrochloride;DL-Cystathionine;535-34-2;DL-Cystathionine dihydrochloride
PubChem CID
439258
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
481.0±45.0 °C at 760 mmHg
Melting Point
312ºC
Flash Point
244.7±28.7 °C
Vapour Pressure
0.0±2.6 mmHg at 25°C
Index of Refraction
1.592
LogP
-0.13
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
7
Heavy Atom Count
14
Complexity
212
Defined Atom Stereocenter Count
2
SMILES
N[C@@H](CCSC[C@H](N)C(O)=O)C(O)=O
InChi Key
ILRYLPWNYFXEMH-WHFBIAKZSA-N
InChi Code
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
Chemical Name
(2S)-2-amino-4-[(2R)-2-amino-2-carboxyethyl]sulfanylbutanoic acid
Synonyms
Cystathionine, L- L-(+)-Cystathionine L-Cystathionine
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
1M HCl : 50 mg/mL (~224.96 mM)
H2O : ~25 mg/mL (~112.48 mM)
DMSO : ~1 mg/mL (~4.50 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 3.33 mg/mL (14.98 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.4994 mL 22.4972 mL 44.9944 mL
5 mM 0.8999 mL 4.4994 mL 8.9989 mL
10 mM 0.4499 mL 2.2497 mL 4.4994 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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