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56-88-2,MFCD00036685
Catalog No.:AA003R5V

56-88-2 | L-Cystathionine

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10mg
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25mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003R5V
Chemical Name:
L-Cystathionine
CAS Number:
56-88-2
Molecular Formula:
C7H14N2O4S
Molecular Weight:
222.2621
MDL Number:
MFCD00036685
SMILES:
N[C@H](C(=O)O)CCSC[C@@H](C(=O)O)N
Properties
Properties
 
Form:
Solid  
MP:
>239°C (dec.)  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
212  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
7  
XLogP3:
-6  

Literature

Title: Cystathionine metabolic enzymes play a role in the inflammation resolution of human keratinocytes in response to sub-cytotoxic formaldehyde exposure.

Journal: Toxicology and applied pharmacology 20161101

Title: Benzyl butyl phthalate promotes adipogenesis in 3T3-L1 preadipocytes: A High Content Cellomics and metabolomic analysis.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20160401

Title: Alterations in hepatic metabolism of sulfur amino acids in non-obese type-2 diabetic Goto-Kakizaki rats.

Journal: Chemico-biological interactions 20130705

Title: Hypothesis with abnormal amino acid metabolism in depression and stress vulnerability in Wistar Kyoto rats.

Journal: Amino acids 20121101

Title: Exploration of the active site of Escherichia coli cystathionine γ-synthase.

Journal: Protein science : a publication of the Protein Society 20121101

Title: Blood biomarkers of methylation in Down syndrome and metabolic simulations using a mathematical model.

Journal: Molecular nutrition & food research 20121001

Title: Cystathionine protects against endoplasmic reticulum stress-induced lipid accumulation, tissue injury, and apoptotic cell death.

Journal: The Journal of biological chemistry 20120914

Title: Methylation capacity in children with severe cerebral palsy.

Journal: European journal of clinical investigation 20120701

Title: Transplant tolerance is associated with reduced expression of cystathionine-γ-lyase that controls IL-12 production by dendritic cells and TH-1 immune responses.

Journal: Blood 20120315

Title: TcyR regulates L-cystine uptake via the TcyABC transporter in Streptococcus mutans.

Journal: FEMS microbiology letters 20120301

Title: New insights into the metabolism of organomercury compounds: mercury-containing cysteine S-conjugates are substrates of human glutamine transaminase K and potent inactivators of cystathionine γ-lyase.

Journal: Archives of biochemistry and biophysics 20120101

Title: Cysteine and obesity: consistency of the evidence across epidemiologic, animal and cellular studies.

Journal: Current opinion in clinical nutrition and metabolic care 20120101

Title: α-Conotoxin ImI incorporating stable cystathionine bridges maintains full potency and identical three-dimensional structure.

Journal: Journal of the American Chemical Society 20111012

Title: RP-HPLC method for quantitative determination of cystathionine, cysteine and glutathione: An application for the study of the metabolism of cysteine in human brain.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110701

Title: Effects of gamma-ray-induced free radicals on the metal content and amino acid composition of human metallothionein-1.

Journal: Journal of biosciences 20110601

Title: Cloning and characterisation of a cystathionine β/γ-lyase from two Oenococcus oeni oenological strains.

Journal: Applied microbiology and biotechnology 20110201

Title: Pre-steady-state kinetic analysis of enzyme-monitored turnover during cystathionine β-synthase-catalyzed H(2)S generation.

Journal: Biochemistry 20110125

Title: A novel transgenic mouse model of CBS-deficient homocystinuria does not incur hepatic steatosis or fibrosis and exhibits a hypercoagulative phenotype that is ameliorated by betaine treatment.

Journal: Molecular genetics and metabolism 20101001

Title: Impaired homocysteine transsulfuration is an indicator of alcoholic liver disease.

Journal: Journal of hepatology 20100901

Title: Residue N84 of yeast cystathionine beta-synthase is a determinant of reaction specificity.

Journal: Biochimica et biophysica acta 20100701

Title: Characterization of site-directed mutants of residues R58, R59, D116, W340 and R372 in the active site of E. coli cystathionine beta-lyase.

Journal: Protein science : a publication of the Protein Society 20100301

Title: Site-directed mutagenesis on human cystathionine-gamma-lyase reveals insights into the modulation of H2S production.

Journal: Journal of molecular biology 20100226

Title: Sulfur amino acids in methionine-restricted rats: hyperhomocysteinemia.

Journal: Nutrition (Burbank, Los Angeles County, Calif.) 20100101

Title: Label-free high-throughput screening via mass spectrometry: a single cystathionine quantitative method for multiple applications.

Journal: Assay and drug development technologies 20091001

Title: Glycine and urea kinetics in nonalcoholic steatohepatitis in human: effect of intralipid infusion.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20090901

Title: Cystathionine gamma-lyase: Clinical, metabolic, genetic, and structural studies.

Journal: Molecular genetics and metabolism 20090801

Title: The metabolomic responses of Caenorhabditis elegans to cadmium are largely independent of metallothionein status, but dominated by changes in cystathionine and phytochelatins.

Journal: Journal of proteome research 20090701

Title: Quantitative profiling of biomarkers related to B-vitamin status, tryptophan metabolism and inflammation in human plasma by liquid chromatography/tandem mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20090501

Title: Multiple strokes in a newborn.

Journal: Ophthalmology 20090401

Title: Moderate dietary vitamin B-6 restriction raises plasma glycine and cystathionine concentrations while minimally affecting the rates of glycine turnover and glycine cleavage in healthy men and women.

Journal: The Journal of nutrition 20090301

Title: Identification and molecular analysis of betaC-S lyase producing hydrogen sulfide in Streptococcus intermedius.

Journal: Journal of medical microbiology 20081101

Title: Properties of recombinant Staphylococcus haemolyticus cystathionine beta-lyase (metC) and its potential role in the generation of volatile thiols in axillary malodor.

Journal: Chemistry & biodiversity 20081101

Title: Modulation of cystathionine beta-synthase activity by the Arg-51 and Arg-224 mutations.

Journal: Bioscience, biotechnology, and biochemistry 20080901

Title: Molecular and enzymatic characterization of betaC-S lyase in Streptococcus constellatus.

Journal: Oral microbiology and immunology 20080601

Title: Iron-dependent formation of homocysteine from methionine and other thioethers.

Journal: European journal of clinical nutrition 20071201

Title: Standardless identification of selenocystathionine and its gamma-glutamyl derivatives in monkeypot nuts by 3D liquid chromatography with ICP-MS detection followed by nanoHPLC-Q-TOF-MS/MS.

Journal: The Analyst 20070501

Title: Biomarkers of folate and vitamin B12 are related in blood and cerebrospinal fluid.

Journal: Clinical chemistry 20070201

Title: Nephroprotective effect of cystathionine is due to its diverse action on the kidney and Ehrlich ascites tumor cells.

Journal: Pharmacological reports : PR 20070101

Title: Different fates of intracellular glutathione determine different modalities of apoptotic nuclear vesiculation.

Journal: Biochemical pharmacology 20061130

Title: A functional transsulfuration pathway in the brain links to glutathione homeostasis.

Journal: The Journal of biological chemistry 20061124

Title: The selective effect of cystathionine on doxorubicin hepatotoxicity in tumor-bearing mice.

Journal: European journal of pharmacology 20061121

Title: Suppression of methionine-induced hyperhomocysteinemia by glycine and serine in rats.

Journal: Bioscience, biotechnology, and biochemistry 20061001

Title: Hyperhomocysteinemia decreases circulating high-density lipoprotein by inhibiting apolipoprotein A-I Protein synthesis and enhancing HDL cholesterol clearance.

Journal: Circulation research 20060915

Title: Modulation of cadmium chloride toxicity by sulphur amino acids in hepatoma cells.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20060801

Title: Soy protein diet prevents hypermethioninemia caused by portacaval shunt in rats.

Journal: The journal of medical investigation : JMI 20060801

Title: A clinical and laboratory evaluation of methionine cycle-transsulfuration and androgen pathway markers in children with autistic disorders.

Journal: Hormone research 20060101

Title: Two newborns with nutritional vitamin B12 deficiency: challenges in newborn screening for vitamin B12 deficiency.

Journal: Haematologica 20051201

Title: Novel mutation in DGUOK in hepatocerebral mitochondrial DNA depletion syndrome associated with cystathioninuria.

Journal: American journal of medical genetics. Part A 20050615

Title: Disturbed homocysteine and methionine cycle intermediates S-adenosylhomocysteine and S-adenosylmethionine are related to degree of renal insufficiency in type 2 diabetes.

Journal: Clinical chemistry 20050501

Title: Inhibitory effect of copper on cystathionine beta-synthase activity: protective effect of an analog of the human albumin N-terminus.

Journal: Protein and peptide letters 20050401

Title: Relationship between S-adenosylmethionine, S-adenosylhomocysteine, asymmetric dimethylarginine, and endothelial function in healthy human subjects during experimental hyper- and hypohomocysteinemia.

Journal: Metabolism: clinical and experimental 20050301

Title: Response of homocysteine, cystathionine, and methylmalonic acid to vitamin treatment in dialysis patients.

Journal: Clinical chemistry 20050101

Title: The enzymology of cystathionine biosynthesis: strategies for the control of substrate and reaction specificity.

Journal: Archives of biochemistry and biophysics 20050101

Title: Cellular uptake of vitamin B12 in patients with chronic renal failure.

Journal: Nephron. Clinical practice 20050101

Title: The relationship between plasma cholesterol, amino acids and acute phase proteins in sepsis.

Journal: Amino acids 20040801

Title: Cystathionine beta-lyase is important for virulence of Salmonella enterica serovar Typhimurium.

Journal: Infection and immunity 20040601

Title: CSF-methionine is elevated in psychotic patients.

Journal: Journal of neural transmission (Vienna, Austria : 1996) 20040501

Title: Influence of hemodialysis membrane permeability on serum levels of advanced glycation end products (AGEs) and homocysteine metabolites.

Journal: Clinical nephrology 20040301

Title: Copper-mediated LDL oxidation by homocysteine and related compounds depends largely on copper ligation.

Journal: Biochimica et biophysica acta 20040120

Title: Cigarette smoke extract increases S-adenosylmethionine and cystathionine in human lung epithelial-like (A549) cells.

Journal: Chemico-biological interactions 20040115

Title: A mathematical model of the methionine cycle.

Journal: Journal of theoretical biology 20040107

Title: Alteration of homocysteine catabolism in pre-eclampsia, HELLP syndrome and placental insufficiency.

Journal: Clinical chemistry and laboratory medicine 20040101

Title: The biosynthesis of cysteine and homocysteine in Methanococcus jannaschii.

Journal: Biochimica et biophysica acta 20031205

Title: Methionine biosynthesis and its regulation in Corynebacterium glutamicum: parallel pathways of transsulfuration and direct sulfhydrylation.

Journal: Applied microbiology and biotechnology 20031001

Title: Effect of acute betaine administration on hepatic metabolism of S-amino acids in rats and mice.

Journal: Biochemical pharmacology 20030501

Title: Genomic basis of cystathioninuria (MIM 219500) revealed by multiple mutations in cystathionine gamma-lyase (CTH).

Journal: Human genetics 20030401

Title: Serum levels of total homocysteine, homocysteine metabolites and of advanced glycation end-products (AGEs) in patients after renal transplantation.

Journal: Clinical nephrology 20030201

Title: Kinetics of the yeast cystathionine beta-synthase forward and reverse reactions: continuous assays and the equilibrium constant for the reaction.

Journal: Biochemistry 20030121

Title: Differences in the betaC-S lyase activities of viridans group streptococci.

Journal: Biochemical and biophysical research communications 20030103

Title: Maternal methionine adenosyltransferase I/III deficiency: reproductive outcomes in a woman with four pregnancies.

Journal: Journal of inherited metabolic disease 20030101

Title: Elevated plasma total homocysteine in severe methionine adenosyltransferase I/III deficiency.

Journal: Metabolism: clinical and experimental 20020801

Title: Synthesis of optically active homocysteine from methionine and its use in preparing four stereoisomers of cystathionine.

Journal: Chemical & pharmaceutical bulletin 20020801

Title: Stopped-flow kinetic analysis of the reaction catalyzed by the full-length yeast cystathionine beta-synthase.

Journal: The Journal of biological chemistry 20020621

Title: Lactobacillus reuteri DSM 20016: purification and characterization of a cystathionine gamma-lyase and use as adjunct starter in cheesemaking.

Journal: The Journal of dairy research 20020501

Title: Molecular characterization of a cystathionine beta-synthase gene, CBS1, in Magnaporthe grisea.

Journal: Eukaryotic cell 20020401

Title: Yeast cystathionine beta-synthase reacts with L-allothreonine, a non-natural substrate, and L-homocysteine to form a new amino acid, 3-methyl-L-cystathionine.

Journal: Biochemistry 20020212

Title: Cystathionine pathway-dependent cytotoxicities of diethyl maleate and diamide in rat and human hepatoma-derived cell cultures.

Journal: Alternatives to laboratory animals : ATLA 20020101

Title: Metabolism of amino acids in cats with severe cobalamin deficiency.

Journal: American journal of veterinary research 20011201

Title: Enhanced cystathionine beta-lyase activity in transgenic potato plants does not force metabolite flow towards methionine.

Journal: Planta 20011201

Title: Decrease of elevated N,N-dimethylglycine and N-methylglycine in human immunodeficiency virus infection during short-term highly active antiretroviral therapy.

Journal: Metabolism: clinical and experimental 20011101

Title: The reaction of yeast cystathionine beta-synthase is rate-limited by the conversion of aminoacrylate to cystathionine.

Journal: Biochemistry 20010911

Title: Homocysteine levels in patients treated with lipid apheresis: effect of a vitamin therapy.

Journal: European journal of clinical investigation 20010801

Title: Genetic defects as important factors for moderate hyperhomocysteinemia.

Journal: Clinical chemistry and laboratory medicine 20010801

Title: Homocysteine, cystathionine, methylmalonic acid and B-vitamins in patients with renal disease.

Journal: Clinical chemistry and laboratory medicine 20010801

Title: Does a single vitamin B-supplementation induce functional vitamin B-deficiency?

Journal: Clinical chemistry and laboratory medicine 20010801

Title: Investigation of relationship between reduced, oxidized, and protein-bound homocysteine and vascular endothelial function in healthy human subjects.

Journal: Circulation research 20010720

Title: Homocysteine metabolism in children with Down syndrome: in vitro modulation.

Journal: American journal of human genetics 20010701

Title: Measurement of intracellular sulfur amino acid metabolism in humans.

Journal: American journal of physiology. Endocrinology and metabolism 20010601

Title: The three-dimensional structure of cystathionine beta-lyase from Arabidopsis and its substrate specificity.

Journal: Plant physiology 20010601

Title: Biosynthesis of methionine from homocysteine, cystathionine and homoserine plus cysteine by mixed rumen microorganisms in vitro.

Journal: Applied microbiology and biotechnology 20010601

Title: Disposition of homocysteine in subjects heterozygous for homocystinuria due to cystathionine beta-synthase deficiency: relationship between genotype and phenotype.

Journal: American journal of medical genetics 20010501

Title: Long-term effects of vitamin B(12), folate, and vitamin B(6) supplements in elderly people with normal serum vitamin B(12) concentrations.

Journal: Gerontology 20010101

Title: Suicide inactivation of bacterial cystathionine gamma-synthase and methionine gamma-lyase during processing of L-propargylglycine.

Journal: Biochemistry 19791016

Title: Effects of glutamate and sulphur containing amino acids on ammonia toxicity and methionine sulphoximine convulsions in mice.

Journal: Brain research 19760618

Title: Xiuli Wang, et al. L-Cystathionine Protects against Homocysteine-Induced Mitochondria-Dependent Apoptosis of Vascular Endothelial Cells. Oxid Med Cell Longev. 2019 Nov 25;2019:1253289.

Title: Amino Y, et al. Synthesis and evaluation of L-cystathionine as a standard for amino acid analysis. Biosci Biotechnol Biochem. 2017 Jan;81(1):95-101.

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Tags:56-88-2 Molecular Formula|56-88-2 MDL|56-88-2 SMILES|56-88-2 L-Cystathionine