(2S)-2-amino-3-hydroxypropanoic acid

• ChemBase编号: 19
• 分子式: C3H7NO3
• 平均质量: 105.09258
• 单一同位素质量: 105.04259309
• SMILES: OC[C@H](N)C(=O)O
• Canonical SMILES: OC[C@@H](C(=O)O)N
• InChI: InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
• InChIKey: MTCFGRXMJLQNBG-REOHCLBHSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-3-hydroxypropanoic acid
• IUPAC传统名: L-serine
• 别名: (S)-2-氨基-3-羟基丙酸; L-丝氨酸; 丝氨酸; H-Ser-OH; L-2-Amino-3-hydroxypropionic acid; (S)-2-Amino-3-hydroxypropanoic acid; Hydroxyalanine; 2-Amino-3-hydroxypropanoic acid; Serine; (-)-Serine; Serine; L-Ser; L-3-Hydroxy-2-aminopropionic acid; L-(-)-Serine; b-Hydroxy-L-alanine; 3-Hydroxyalanine; 2-Amino-3-hydroxypropionic acid; (S)-Serine; (S)-a-Amino-b-hydroxypropionic acid; (S)-2-Amino-3-hydroxypropanoic acid; L-Serine; beta-HYDROXYALANINE; L-SERINE, USP GRADE; L-Serine; (S)-2-Amino-3-hydroxypropionic acid; Serinum

登记号

• CAS号: 56-45-1
• EC号: 206-130-6; 200-274-3
• MDL号: MFCD00064224
• Beilstein号: 1721404
• 默克索引号: 148460
• PubChem SID: 24899473; 24899605; 24888286; 24887156; 160963482; 24899599; 46506450
• PubChem CID: 617; 5951
• CHEBI ID: 17115
• CHEMBL: 11298
• Chemspider ID: 5736
• DrugBank ID: DB00133
• IUPHAR配体索引: 726
• 美国药典/FDA物质标识码: 452VLY9402
• 维基百科标题: Serine

理论计算性质

JChem

• Acid pKa: 2.03399
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): -3.8875728
• LogD (pH = 7.4): -3.8992038
• Log P: -3.8877351
• 摩尔折射率: 22.041 cm^3
• 极化性: 9.0643015 Å^3
• 极化表面积: 83.55 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: -3.42
• LOG S: 0.66
• 溶解度: 4.80e+02 g/l

分子性质

理化性质

• 溶解度: 1 M HCl: soluble0.5 M at 20 °C, clear, colorless; 425 g/L; H2O: soluble50 mg/mL; soluble in water
• 外观: powder; white crystals or powder
• 熔点: > 228°C; 214-224°C dec.; 222 °C (dec.)(lit.); 246 °C decomp.
• 密度: 1.603 g/cm^3 (22 °C)
• 比旋光度: [α]20/D +13±0.5°, c = 5% in 5 M HCl; [α]20/D +13±1°, c = 5% in 5 M HCl; +15 (c=9 in 1N HCl)
• 紫外吸收波长: λ: 260 nm Amax: 0.05; λ: 280 nm Amax: 0.05
• 疏水性(logP): -4
• pKa: 2.21 (carboxyl), 9.15 (amino)

安全信息

• 保存条件: Room Temperature (15-30°C)
• 保存注意事项: IRRITANT
• RTECS编号: VT8100000
• 德国WGK号: 1
• TSCA收录: false; 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: ≥99%; ≥98.5%; ≥99% (TLC); ≥99.0% (NT); ≥99.5% (NT); 95+%; 97%; 98%; 98.5-101.0%; 99%
• 级别: certified reference material; EP; Ph Eur; PharmaGrade; ReagentPlus®; TraceCERT®; USP
• 适用性: meets EP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• 燃烧残渣: ≤0.1% (as SO4)
• 杂质: ≤0.3% foreign amino acids; ≤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: ≤50 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: ≤50 mg/kg; NH4+: ≤100 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-): ≤50 mg/kg; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤50 mg/kg
• 生物来源: from non-animal source
• 有效期: (limited shelf life, expiry date on the label)
• 干燥失重: ≤0.1% loss on drying, 20 °C (HV); ≤0.2% loss on drying, 110 °C
• 产品质量级别: GMP-COMPENDIA
• λ: 0.5 M in 1 M HCl
• 药典: testing & handling conforms to Pharmacopeia
• 产品线: BioUltra
• 线性分子式: HOCH2CH(NH2)CO2H

详细说明

MP Biomedicals - 02199560

White powder

MP Biomedicals - 02194737

Cell Culture Reagent
Purity: 99+%
Crystalline

MP Biomedicals - 02102873

Purity: 99+%
Crystalline

DrugBank - DB03375

Drug information: experimental

DrugBank - DB00133

• Drug Groups: approved; nutraceutical
• Description: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from glycine or threonine. It is involved in the biosynthesis of purines; pyrimidines; and other amino acids. [PubChem]
• Indication: Used as a natural moisturizing agent in some cosmetics and skin care products.
• Pharmacology: Serine is classified as a nutritionally non-essential amino acid. Serine is critical for the production of the body's proteins, enzymes and muscle tissue. Serine is needed for the proper metabolism of fats and fatty acids. It also helps in the production of antibodies. Serine is used as a natural moisturizing agent in some cosmetics and skin care products. The main source of essential amino acids is from the diet, non-essential amino acids are normally synthesize by humans and other mammals from common intermediates.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Sigma Aldrich - S4311

Biochem/physiol Actions
通过丝氨酸羟甲基转移酶获得甘氨酸时的前体。

Sigma Aldrich - S1315

Biochem/physiol Actions
通过丝氨酸羟甲基转移酶获得甘氨酸时的前体。
包装
根据 cGMP 制造和包装。

Sigma Aldrich - S4500

Biochem/physiol Actions
通过丝氨酸羟甲基转移酶获得甘氨酸时的前体。
包装
1 kg in poly bottle
1, 100 g in poly bottle
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 84959

Biochem/physiol Actions
通过丝氨酸羟甲基转移酶获得甘氨酸时的前体。
Other Notes
Synthesis of labels for protonation studies by Fourier Transform infrared methods1; Stabilizes mung bean nuclease at pH values below seven2; Amino acid spacing in isotachophoresis on polyacrylamide gel - a critical evaluation3; Growth requirement of various microorganisms4

Sigma Aldrich - 78682

Biochem/physiol Actions
通过丝氨酸羟甲基转移酶获得甘氨酸时的前体。

Sigma Aldrich - 54763

Analysis Note
此认证标准物质 (CRM) 的生产和认证都符合 ISO/IEC 17025 和 ISO Guide 34 的要求。此 CRM 可溯源到 NIST SRM。
Biochem/physiol Actions
通过丝氨酸羟甲基转移酶获得甘氨酸时的前体。
General description
认证的含量经定量 NMR 确定，并且证书上标明不确定度和有效期。 证书下载：http://www.sigma-aldrich.com。
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 84960

Biochem/physiol Actions
通过丝氨酸羟甲基转移酶获得甘氨酸时的前体。

参考文献

• Has been used in a synthesis of D-amino acids. The configuration is inverted by conversion of the carboxyl group to the new alkyl chain by reaction with an organolithium reagent to give the ketone, which is deoxygenated by Raney nickel desulfurization of the thioketal, the hydroxymethyl group becoming the new carboxyl group by oxidation with oxygen over a Pt catalyst: J. Am. Chem. Soc., 106, 1095 (1984):