(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid

• ChemBase编号: 24
• 分子式: C6H12N2O4S2
• 平均质量: 240.30048
• 单一同位素质量: 240.02384887
• SMILES: S(SC[C@H](N)C(=O)O)C[C@H](N)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)CSSC[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1
• InChIKey: LEVWYRKDKASIDU-IMJSIDKUSA-N

名称和登记号

名称

• IUPAC标准名: (2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid
• IUPAC传统名: L-cystine
• 别名: (R,R)-3,3′-二硫双(2-氨基丙酸); L-胱氨酸; L-Cystine; Dicysteine; 3,3'-Dithiobis (2-aminopropanoic acid); Cystein disulfide; 3,3'-Dithiobis(2-aminopropanoic Acid); Bis(β-amino-β-carboxyethyl) Disulfide; Cystine Αcid; 3,3'-Dithiobis-L-Alanine; L-Cysteine Disulfide; L-Cystin; NSC 13203; Oxidized L-cysteine; [R-(R*,R*)]-3,3'-Dithiobis[2-aminopropanoic Acid]; l-Cystine; β,β'-Diamino-β,β'-dicarboxydiethyl Disulfide; β,β'-Dithiodialanine; (-)-Cystine; Cysteine disulfide; Cystine acid; L-alpha-Diamino-beta-dithiolactic acid; L-Dicysteine; L-Cystine; (R,R)-3,3′-Dithiobis(2-aminopropionicacid); H-(Cys)2-OH; (-)-3,3'-Dithiobis(2-aminopropionic acid)

登记号

• CAS号: 56-89-3
• EC号: 200-296-3
• MDL号: MFCD00064228
• Beilstein号: 1728094
• 默克索引号: 142782
• PubChem SID: 160963487; 24893101; 24892581; 24892973; 46506670; 24858224
• PubChem CID: 67678
• E编码: E921

理论计算性质

JChem

• Acid pKa: 1.5564231
• 质子受体: 6
• 质子供体: 4
• LogD (pH = 5.5): -5.897319
• LogD (pH = 7.4): -5.9155164
• Log P: -5.897688
• 摩尔折射率: 54.8718 cm^3
• 极化性: 22.177225 Å^3
• 极化表面积: 126.64 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -3.16
• LOG S: -1.16
• 溶解度: 1.68e+01 g/l

分子性质

理化性质

• 溶解度: 1 M HCl: soluble0.2 M at 20 °C, clear, colorless; 1 M HCl: soluble100 mg/mL; Soluble
• 外观: crystalline; powder
• 熔点: >240 °C (dec.)(lit.); >240°C dec.; 260 - 261°C
• 密度: 1.68
• 比旋光度: [α]20/D -217.8°, c = 1 in 1 M HCl; [α]20/D -219±5°, c = 1% in 1 M HCl; -219 (c=1 in 1N HCl)
• 疏水性(logP): -5.5

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: HA2690000
• 德国WGK号: 3
• TSCA收录: 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥98% (TLC); ≥98.5%; ≥99.0%; ≥99.5% (T); 97%; 98.5-101.0%; 99%
• 级别: certified reference material; EP; SAJ special grade; TraceCERT®
• 适用性: meets EP testing specifications; suitable for cell culture; suitable for manufacturing use
• 燃烧残渣: ≤0.05% (as SO4)
• 杂质: ≤0.3% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• 痕量阳离子: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤10 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• 痕量阴离子: chloride (Cl-): ≤500 mg/kg; sulfate (SO42-): ≤100 mg/kg
• 生物来源: from non-animal source
• 干燥失重: ≤0.05% loss on drying, 20 °C (HV)
• 产品质量级别: GMP-COMPENDIA
• 产品线: BioUltra
• abs.: absorption0.2M/316 nm, 1 M HCl cut-off
• 线性分子式: [-SCH2CH(NH2)CO2H]2

详细说明

MP Biomedicals - 05202117

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02194649

Cell Culture Reagent Purity: 99% White crystals

MP Biomedicals - 02101454

Purity: 99%
White crystals

DrugBank - DB00138

• Drug Groups: approved; nutraceutical
• Description: A covalently linked dimeric nonessential amino acid formed by the oxidation of cysteine. Two molecules of cysteine are joined together by a disulfide bridge to form cystine. [PubChem]
• Indication: It has been claimed that L-cysteine has anti-inflammatory properties, that it can protect against various toxins, and that it might be helpful in osteoarthritis and rheumatoid arthritis. More research will have to be done before L-cysteine can be indicated for any of these conditions. Research to date has mostly been in animal models.
• Pharmacology: L-Cystine is a covalently linked dimeric nonessential amino acid formed by the oxidation of cysteine. Two molecules of cysteine are joined together by a disulfide bridge to form cystine. Cystine is a chemical substance which naturally occurs as a deposit in the urine, and can form a calculus (hard mineral formation) when deposited in the kidney. The compound produced when two cysteine molecules linked by a disulfide (S-S) bond. Cystine is required for proper vitamin B6 utilization and is also helpful in the healing of burns and wounds, breaking down mucus deposits in illnesses such as bronchitis as well as cystic fibrosis. Cysteine also assists in the supply of insulin to the pancreas, which is needed for the assimilation of sugars and starches. It increases the level of glutathione in the lungs, liver, kidneys and bone marrow, and this may have an anti-aging effect on the body by reducing age-spots etc.
• Toxicity: With typical doses of 1 to 1.5 grams daily, the most commonly reported side effects have been gastrointestinal, such as nausea. There are rare reports of cystine renal stone formation, Single injections of L-cysteine (0.6-1.5 g/kg) into 4-day-old pups resulted in massive damage to cortical neurons, permanent retinal dystrophy, atrophy of the brain and hyperactivity.
• Affected Organisms: Humans and other mammals
• External Links: PDRhealth

Sigma Aldrich - C8755

包装
100, 500 g in poly bottle

Sigma Aldrich - C7602

包装
10 mg in autosmp vl
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7602.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7602.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - C5735

包装
根据 cGMP 制造和包装

Sigma Aldrich - 30199

Other Notes
Certain malignant cell lines require cystine or cysteine in the culture medium1; Growth requirement of various microorganisms2

Sigma Aldrich - C122009

包装
2.5 g in glass bottle

Sigma Aldrich - 49603

Analysis Note
该有证标准物质 (CRM) 根据 ISO/IEC 17025 和 ISO 指南 34 生产和认证。该有证标准物质可溯源到 NIST 标准参考物质。
General description
证书上给出了含不确定度的认证含量（定量 NMR 法测定）和有效期。 证书下载：http://www.sigma-aldrich.com。
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - C997860

L-Cystine is a non-essential amino acid for human development. L-Cystine is formed by the dimerization of two cysteines through the sulfur.

参考文献

• Fahey, R.C., et al.: J. Mol. Evol., 10, 155 (1977)
• Kao, P., et al.: J. Biol.Chem., 261, 8085 ( 1986), Nicke, A., et al.: J. Biol. Chem., 278, 3137 (1977)