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56-88-2 | L-Cystathionine
CAS No: 56-88-2 Catalog No: AG003R8N MDL No:
Product Description
Catalog Number:
AG003R8N
Chemical Name:
L-Cystathionine
CAS Number:
56-88-2
Molecular Formula:
C7H14N2O4S
Molecular Weight:
222.2621
IUPAC Name:
(2S)-2-amino-4-[(2R)-2-amino-2-carboxyethyl]sulfanylbutanoic acid
InChI:
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
SMILES:
N[C@H](C(=O)O)CCSC[C@@H](C(=O)O)N
EC Number:
200-295-8
UNII:
375YFJ481O
Properties
Complexity:
212
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
2
Defined Bond Stereocenter Count:
0
Exact Mass:
222.067g/mol
Formal Charge:
0
Heavy Atom Count:
14
Hydrogen Bond Acceptor Count:
7
Hydrogen Bond Donor Count:
4
Isotope Atom Count:
0
Molecular Weight:
222.259g/mol
Monoisotopic Mass:
222.067g/mol
Rotatable Bond Count:
7
Topological Polar Surface Area:
152A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-6
Literature
| Title | Journal |
|---|---|
| Cystathionine metabolic enzymes play a role in the inflammation resolution of human keratinocytes in response to sub-cytotoxic formaldehyde exposure. | Toxicology and applied pharmacology 20161101 |
| Benzyl butyl phthalate promotes adipogenesis in 3T3-L1 preadipocytes: A High Content Cellomics and metabolomic analysis. | Toxicology in vitro : an international journal published in association with BIBRA 20160401 |
| Alterations in hepatic metabolism of sulfur amino acids in non-obese type-2 diabetic Goto-Kakizaki rats. | Chemico-biological interactions 20130705 |
| Hypothesis with abnormal amino acid metabolism in depression and stress vulnerability in Wistar Kyoto rats. | Amino acids 20121101 |
| Exploration of the active site of Escherichia coli cystathionine γ-synthase. | Protein science : a publication of the Protein Society 20121101 |
| Blood biomarkers of methylation in Down syndrome and metabolic simulations using a mathematical model. | Molecular nutrition & food research 20121001 |
| Cystathionine protects against endoplasmic reticulum stress-induced lipid accumulation, tissue injury, and apoptotic cell death. | The Journal of biological chemistry 20120914 |
| Methylation capacity in children with severe cerebral palsy. | European journal of clinical investigation 20120701 |
| Transplant tolerance is associated with reduced expression of cystathionine-γ-lyase that controls IL-12 production by dendritic cells and TH-1 immune responses. | Blood 20120315 |
| TcyR regulates L-cystine uptake via the TcyABC transporter in Streptococcus mutans. | FEMS microbiology letters 20120301 |
| 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. | Archives of biochemistry and biophysics 20120101 |
| Cysteine and obesity: consistency of the evidence across epidemiologic, animal and cellular studies. | Current opinion in clinical nutrition and metabolic care 20120101 |
| α-Conotoxin ImI incorporating stable cystathionine bridges maintains full potency and identical three-dimensional structure. | Journal of the American Chemical Society 20111012 |
| 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 of chromatography. B, Analytical technologies in the biomedical and life sciences 20110701 |
| Effects of gamma-ray-induced free radicals on the metal content and amino acid composition of human metallothionein-1. | Journal of biosciences 20110601 |
| Cloning and characterisation of a cystathionine β/γ-lyase from two Oenococcus oeni oenological strains. | Applied microbiology and biotechnology 20110201 |
| Pre-steady-state kinetic analysis of enzyme-monitored turnover during cystathionine β-synthase-catalyzed H(2)S generation. | Biochemistry 20110125 |
| 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. | Molecular genetics and metabolism 20101001 |
| Impaired homocysteine transsulfuration is an indicator of alcoholic liver disease. | Journal of hepatology 20100901 |
| Residue N84 of yeast cystathionine beta-synthase is a determinant of reaction specificity. | Biochimica et biophysica acta 20100701 |
| Characterization of site-directed mutants of residues R58, R59, D116, W340 and R372 in the active site of E. coli cystathionine beta-lyase. | Protein science : a publication of the Protein Society 20100301 |
| Site-directed mutagenesis on human cystathionine-gamma-lyase reveals insights into the modulation of H2S production. | Journal of molecular biology 20100226 |
| Sulfur amino acids in methionine-restricted rats: hyperhomocysteinemia. | Nutrition (Burbank, Los Angeles County, Calif.) 20100101 |
| Label-free high-throughput screening via mass spectrometry: a single cystathionine quantitative method for multiple applications. | Assay and drug development technologies 20091001 |
| Glycine and urea kinetics in nonalcoholic steatohepatitis in human: effect of intralipid infusion. | American journal of physiology. Gastrointestinal and liver physiology 20090901 |
| Cystathionine gamma-lyase: Clinical, metabolic, genetic, and structural studies. | Molecular genetics and metabolism 20090801 |
| The metabolomic responses of Caenorhabditis elegans to cadmium are largely independent of metallothionein status, but dominated by changes in cystathionine and phytochelatins. | Journal of proteome research 20090701 |
| Quantitative profiling of biomarkers related to B-vitamin status, tryptophan metabolism and inflammation in human plasma by liquid chromatography/tandem mass spectrometry. | Rapid communications in mass spectrometry : RCM 20090501 |
| Multiple strokes in a newborn. | Ophthalmology 20090401 |
| 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. | The Journal of nutrition 20090301 |
| Identification and molecular analysis of betaC-S lyase producing hydrogen sulfide in Streptococcus intermedius. | Journal of medical microbiology 20081101 |
| Properties of recombinant Staphylococcus haemolyticus cystathionine beta-lyase (metC) and its potential role in the generation of volatile thiols in axillary malodor. | Chemistry & biodiversity 20081101 |
| Modulation of cystathionine beta-synthase activity by the Arg-51 and Arg-224 mutations. | Bioscience, biotechnology, and biochemistry 20080901 |
| Molecular and enzymatic characterization of betaC-S lyase in Streptococcus constellatus. | Oral microbiology and immunology 20080601 |
| Iron-dependent formation of homocysteine from methionine and other thioethers. | European journal of clinical nutrition 20071201 |
| 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. | The Analyst 20070501 |
| Biomarkers of folate and vitamin B12 are related in blood and cerebrospinal fluid. | Clinical chemistry 20070201 |
| Nephroprotective effect of cystathionine is due to its diverse action on the kidney and Ehrlich ascites tumor cells. | Pharmacological reports : PR 20070101 |
| Different fates of intracellular glutathione determine different modalities of apoptotic nuclear vesiculation. | Biochemical pharmacology 20061130 |
| A functional transsulfuration pathway in the brain links to glutathione homeostasis. | The Journal of biological chemistry 20061124 |
| The selective effect of cystathionine on doxorubicin hepatotoxicity in tumor-bearing mice. | European journal of pharmacology 20061121 |
| Suppression of methionine-induced hyperhomocysteinemia by glycine and serine in rats. | Bioscience, biotechnology, and biochemistry 20061001 |
| Hyperhomocysteinemia decreases circulating high-density lipoprotein by inhibiting apolipoprotein A-I Protein synthesis and enhancing HDL cholesterol clearance. | Circulation research 20060915 |
| Modulation of cadmium chloride toxicity by sulphur amino acids in hepatoma cells. | Toxicology in vitro : an international journal published in association with BIBRA 20060801 |
| Soy protein diet prevents hypermethioninemia caused by portacaval shunt in rats. | The journal of medical investigation : JMI 20060801 |
| A clinical and laboratory evaluation of methionine cycle-transsulfuration and androgen pathway markers in children with autistic disorders. | Hormone research 20060101 |
| Two newborns with nutritional vitamin B12 deficiency: challenges in newborn screening for vitamin B12 deficiency. | Haematologica 20051201 |
| Novel mutation in DGUOK in hepatocerebral mitochondrial DNA depletion syndrome associated with cystathioninuria. | American journal of medical genetics. Part A 20050615 |
| Disturbed homocysteine and methionine cycle intermediates S-adenosylhomocysteine and S-adenosylmethionine are related to degree of renal insufficiency in type 2 diabetes. | Clinical chemistry 20050501 |
| Inhibitory effect of copper on cystathionine beta-synthase activity: protective effect of an analog of the human albumin N-terminus. | Protein and peptide letters 20050401 |
| Relationship between S-adenosylmethionine, S-adenosylhomocysteine, asymmetric dimethylarginine, and endothelial function in healthy human subjects during experimental hyper- and hypohomocysteinemia. | Metabolism: clinical and experimental 20050301 |
| Response of homocysteine, cystathionine, and methylmalonic acid to vitamin treatment in dialysis patients. | Clinical chemistry 20050101 |
| The enzymology of cystathionine biosynthesis: strategies for the control of substrate and reaction specificity. | Archives of biochemistry and biophysics 20050101 |
| Cellular uptake of vitamin B12 in patients with chronic renal failure. | Nephron. Clinical practice 20050101 |
| The relationship between plasma cholesterol, amino acids and acute phase proteins in sepsis. | Amino acids 20040801 |
| Cystathionine beta-lyase is important for virulence of Salmonella enterica serovar Typhimurium. | Infection and immunity 20040601 |
| CSF-methionine is elevated in psychotic patients. | Journal of neural transmission (Vienna, Austria : 1996) 20040501 |
| Influence of hemodialysis membrane permeability on serum levels of advanced glycation end products (AGEs) and homocysteine metabolites. | Clinical nephrology 20040301 |
| Copper-mediated LDL oxidation by homocysteine and related compounds depends largely on copper ligation. | Biochimica et biophysica acta 20040120 |
| Cigarette smoke extract increases S-adenosylmethionine and cystathionine in human lung epithelial-like (A549) cells. | Chemico-biological interactions 20040115 |
| A mathematical model of the methionine cycle. | Journal of theoretical biology 20040107 |
| Alteration of homocysteine catabolism in pre-eclampsia, HELLP syndrome and placental insufficiency. | Clinical chemistry and laboratory medicine 20040101 |
| The biosynthesis of cysteine and homocysteine in Methanococcus jannaschii. | Biochimica et biophysica acta 20031205 |
| Methionine biosynthesis and its regulation in Corynebacterium glutamicum: parallel pathways of transsulfuration and direct sulfhydrylation. | Applied microbiology and biotechnology 20031001 |
| Effect of acute betaine administration on hepatic metabolism of S-amino acids in rats and mice. | Biochemical pharmacology 20030501 |
| Genomic basis of cystathioninuria (MIM 219500) revealed by multiple mutations in cystathionine gamma-lyase (CTH). | Human genetics 20030401 |
| Serum levels of total homocysteine, homocysteine metabolites and of advanced glycation end-products (AGEs) in patients after renal transplantation. | Clinical nephrology 20030201 |
| Kinetics of the yeast cystathionine beta-synthase forward and reverse reactions: continuous assays and the equilibrium constant for the reaction. | Biochemistry 20030121 |
| Differences in the betaC-S lyase activities of viridans group streptococci. | Biochemical and biophysical research communications 20030103 |
| Maternal methionine adenosyltransferase I/III deficiency: reproductive outcomes in a woman with four pregnancies. | Journal of inherited metabolic disease 20030101 |
| Elevated plasma total homocysteine in severe methionine adenosyltransferase I/III deficiency. | Metabolism: clinical and experimental 20020801 |
| Synthesis of optically active homocysteine from methionine and its use in preparing four stereoisomers of cystathionine. | Chemical & pharmaceutical bulletin 20020801 |
| Stopped-flow kinetic analysis of the reaction catalyzed by the full-length yeast cystathionine beta-synthase. | The Journal of biological chemistry 20020621 |
| Lactobacillus reuteri DSM 20016: purification and characterization of a cystathionine gamma-lyase and use as adjunct starter in cheesemaking. | The Journal of dairy research 20020501 |
| Molecular characterization of a cystathionine beta-synthase gene, CBS1, in Magnaporthe grisea. | Eukaryotic cell 20020401 |
| 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. | Biochemistry 20020212 |
| Cystathionine pathway-dependent cytotoxicities of diethyl maleate and diamide in rat and human hepatoma-derived cell cultures. | Alternatives to laboratory animals : ATLA 20020101 |
| Metabolism of amino acids in cats with severe cobalamin deficiency. | American journal of veterinary research 20011201 |
| Enhanced cystathionine beta-lyase activity in transgenic potato plants does not force metabolite flow towards methionine. | Planta 20011201 |
| Decrease of elevated N,N-dimethylglycine and N-methylglycine in human immunodeficiency virus infection during short-term highly active antiretroviral therapy. | Metabolism: clinical and experimental 20011101 |
| The reaction of yeast cystathionine beta-synthase is rate-limited by the conversion of aminoacrylate to cystathionine. | Biochemistry 20010911 |
| Homocysteine levels in patients treated with lipid apheresis: effect of a vitamin therapy. | European journal of clinical investigation 20010801 |
| Genetic defects as important factors for moderate hyperhomocysteinemia. | Clinical chemistry and laboratory medicine 20010801 |
| Homocysteine, cystathionine, methylmalonic acid and B-vitamins in patients with renal disease. | Clinical chemistry and laboratory medicine 20010801 |
| Does a single vitamin B-supplementation induce functional vitamin B-deficiency? | Clinical chemistry and laboratory medicine 20010801 |
| Investigation of relationship between reduced, oxidized, and protein-bound homocysteine and vascular endothelial function in healthy human subjects. | Circulation research 20010720 |
| Homocysteine metabolism in children with Down syndrome: in vitro modulation. | American journal of human genetics 20010701 |
| Measurement of intracellular sulfur amino acid metabolism in humans. | American journal of physiology. Endocrinology and metabolism 20010601 |
| The three-dimensional structure of cystathionine beta-lyase from Arabidopsis and its substrate specificity. | Plant physiology 20010601 |
| Biosynthesis of methionine from homocysteine, cystathionine and homoserine plus cysteine by mixed rumen microorganisms in vitro. | Applied microbiology and biotechnology 20010601 |
| Disposition of homocysteine in subjects heterozygous for homocystinuria due to cystathionine beta-synthase deficiency: relationship between genotype and phenotype. | American journal of medical genetics 20010501 |
| Long-term effects of vitamin B(12), folate, and vitamin B(6) supplements in elderly people with normal serum vitamin B(12) concentrations. | Gerontology 20010101 |
| Suicide inactivation of bacterial cystathionine gamma-synthase and methionine gamma-lyase during processing of L-propargylglycine. | Biochemistry 19791016 |
| Effects of glutamate and sulphur containing amino acids on ammonia toxicity and methionine sulphoximine convulsions in mice. | Brain research 19760618 |
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