(2R)-2-amino-3-sulfanylpropanoic acid

• ChemBase编号: 37
• 分子式: C3H7NO2S
• 平均质量: 121.15818
• 单一同位素质量: 121.01974947
• SMILES: SC[C@H](N)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)CS
• InChI: InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
• InChIKey: XUJNEKJLAYXESH-REOHCLBHSA-N

名称和登记号

名称

• IUPAC标准名: (2R)-2-amino-3-sulfanylpropanoic acid
• IUPAC传统名: L-cysteine
• 别名: L半胱氨酸; (R)-2-氨基-3-巯基丙酸; L-半胱氨酸; Cysteine; E 920; NSC 8746; β-Mercaptoalanine; H-Cys-OH; (R)-2-amino-3-mercaptopropanoic acid; 2-Amino-3-sulfhydrylpropanoic acid; Cysteine; (R)-2-Amino-3-mercaptopropionic acid; L-Cysteine; β-Mercapto-L-alanine; L-CYSTEINE FREE BASE; (2R)-2-Amino-3-sulphanylpropanoic acid; (2R)-2-Amino-3-mercaptopropionic acid; (2R)-2-Amino-3-mercaptopropanoic acid; L-2-Amino-3-mercaptopropionic acid; 3-mercapto-L-Alanine; L-Cys; L-(+)-Cysteine; Half-cystine; Thioserine; Cystein; Cys; carbocysteine; b-Mercaptoalanine; 2-Amino-3-mercaptopropionic acid; (R)-Cysteine; (R)-2-Amino-3-mercaptopropanoic acid; L-Cysteine; Free Cysteine

登记号

• CAS号: 52-90-4
• EC号: 200-158-2
• MDL号: MFCD00064306
• Beilstein号: 1721408
• 默克索引号: 142781
• PubChem SID: 24892959; 160963500; 24858110; 24901592; 46506553; 24892777; 24850236
• PubChem CID: 5862
• CHEBI ID: 15356
• CHEMBL: 54943
• Chemspider ID: 574
• FEMA编号: 3263
• KEGG ID: D00026
• 美国药典/FDA物质标识码: K848JZ4886
• 维基百科标题: Cysteine
• Flavis Number: 17.033
• E编码: E920

理论计算性质

JChem

• Acid pKa: 2.3459952
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): -2.7920592
• LogD (pH = 7.4): -2.8006835
• Log P: -2.7921333
• 摩尔折射率: 28.2236 cm^3
• 极化性: 11.415023 Å^3
• 极化表面积: 63.32 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -2.57
• LOG S: -0.72
• 溶解度: 2.31e+01 g/l

分子性质

理化性质

• 溶解度: 1 M HCl: soluble1 M at 20 °C, clear, colorless; 1.5g/100g ethanol 19 degC; 277 mg/mL at 25 oC [BEILSTEIN]; H2O: soluble25 mg/mL; soluble in water
• 外观: white crystals or powder
• 熔点: 220 °C (dec.)(lit.); 240 °C decomp.; 240(dec.)°C; ca 220°C dec.; decomposes 175-178 °C
• 比旋光度: [α]20/D +6.5±1.5°, c = 2 in 5 M HCl; [α]20/D +7.6±0.5°, c = 5% in 5 M HCl; [α]20/D +8.0±0.5°, c = 5% in 5 M HCl; [α]26/D +8.0 to +9.5°, c = 2 in 5 M HCl; +7.9 (c=5 in 5N HCl); +9.4° (H₂O, c = 1.3)
• 紫外吸收波长: λ: 260 nm Amax: 1.5; λ: 280 nm Amax: 0.2
• 疏水性(logP): -2.6

安全信息

• 保存条件: Room Temperature (15-30°C), Desiccate, Store Under Nitrogen
• 保存注意事项: Air Sensitive; Harmful/Irritant/Air Sensitive/Store under Argon
• RTECS编号: HA1600000
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 德国WGK号: 1
• 危险公开号: 22; R:22-36/37/38
• 安全公开号: 36/37; S:25-26-36/37/39
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• GHS警示性声明: P264-P270-P301+P312-P330-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 20-25°C; 2-8°C

产品相关信息

• 纯度: ≥97%; ≥98%; ≥98.5%; ≥98.5% (RT); 97%; 98%; 98+%
• 级别: certified reference material; EP; NI; PharmaGrade; SAJ special grade; TraceCERT®; USP
• 光学纯度: ee: 96% (GLC)
• 适用性: suitable for cell culture; suitable for manufacturing use
• 燃烧残渣: ≤0.05% (as SO4); ≤0.1% (as SO4)
• 杂质: ≤0.5% 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: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤100 mg/kg; NH4+: ≤500 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-): ≤100 mg/kg; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤50 mg/kg
• 生物来源: from non-animal source
• 干燥失重: ≤0.05% loss on drying, 20 °C (HV); ≤0.1% loss on drying, 110 °C
• 产品质量级别: GMP-COMPENDIA
• λ: 1 M in 1 M HCl
• 产品线: BioReagent; BioUltra
• 线性分子式: HSCH2CH(NH2)CO2H

详细说明

MP Biomedicals - 02101444

Free Base
Crystalline

MP Biomedicals - 02194646

Free Base
Cell Culture Reagent
Crystalline

DrugBank - DB04443

Drug information: experimental

DrugBank - DB00151

• Drug Groups: approved; nutraceutical
• Description: A thiol-containing non-essential amino acid that is oxidized to form cystine. [PubChem]
• Indication: For the prevention of liver damage and kidney damage associated with overdoses of acetaminophen
• Pharmacology: Due to this ability to undergo redox reactions, cysteine has antioxidant properties. Cysteine is an important source of sulfur in human metabolism, and although it is classified as a non-essential amino acid, cysteine may be essential for infants, the elderly, and individuals with certain metabolic disease or who suffer from malabsorption syndromes. Cysteine may at some point be recognized as an essential or conditionally essential amino acid.
• Affected Organisms: Humans and other mammals
• References: Bulaj G, Kortemme T, Goldenberg DP: Ionization-reactivity relationships for cysteine thiols in polypeptides. Biochemistry. 1998 Jun 23;37(25):8965-72. [Pubmed] ; Baker DH, Czarnecki-Maulden GL: Pharmacologic role of cysteine in ameliorating or exacerbating mineral toxicities. J Nutr. 1987 Jun;117(6):1003-10. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - C7352

Biochem/physiol Actions
NMDA 谷氨酸受体激动剂。
Other Notes
L-Cysteine is used to supplement cell culture media. This product is a non-animal source amino acid useful for serum-free media formulations intended for biomanufacturing applications.
包装
10 mg in autosmp vl
General description
L-Cysteine is a proteinogenic amino acid incorporated into proteins as directed by the genetic code. The thiol-side chain participates in a variety of oxidation/reduction reactions within the cell. The side chain participates in the formation of β bonds that modulate the secondary and ternary structure of proteins. Cysteine is essential and limiting for the formation of glutathione, an important antioxidant, within the cell.

Sigma Aldrich - 30089

Biochem/physiol Actions
NMDA 谷氨酸受体激动剂。

Sigma Aldrich - C5360

Biochem/physiol Actions
NMDA 谷氨酸受体激动剂。
Quality
Manufactured and Packaged under cGMP

Sigma Aldrich - 168149

Biochem/physiol Actions
NMDA 谷氨酸受体激动剂。
General description
天然存在的非必需氨基酸。
包装
2.5 g in glass bottle
2.5 kg in poly bottle
25, 100, 500 g in poly bottle

Sigma Aldrich - W326305

Biochem/physiol Actions
NMDA 谷氨酸受体激动剂。
包装
1 kg in poly bottle
1 sample in glass bottle
100 g in poly bottle
5 kg in fiber drum

Sigma Aldrich - 95437

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。
Biochem/physiol Actions
NMDA 谷氨酸受体激动剂。
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

Sigma Aldrich - 30090

Biochem/physiol Actions
NMDA 谷氨酸受体激动剂。

Sigma Aldrich - 05-7460

Biochem/physiol Actions
NMDA 谷氨酸受体激动剂。

Toronto Research Chemicals - C995000

L-Cysteine is a non-essential amino acid that can be synthesized by the human body under normal physiological conditions if a sufficient quantity of methionine is available. L-Cysteine is commonly used as a precursor in the food and pharmaceutical industr

参考文献

• Bulaj G, Kortemme T, Goldenberg DP: Ionization-reactivity relationships for cysteine thiols in polypeptides. Biochemistry. 1998 Jun 23;37(25):8965-72. Pubmed
• Baker DH, Czarnecki-Maulden GL: Pharmacologic role of cysteine in ameliorating or exacerbating mineral toxicities. J Nutr. 1987 Jun;117(6):1003-10. Pubmed
• Pecivova, P. et al.: J. Sci. Food Agric., 90, 1681 (2010)
• Hui, N. et al.: Meat Sci. Appl., 74 (2010)
• Kiviharju, K. et al.: J. Biotechnol., 117, 299 (2010)