(2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid

• ChemBase编号: 132377
• 分子式: C5H9NO3
• 平均质量: 131.12986
• 单一同位素质量: 131.05824315
• SMILES: C1[C@@H](CN[C@@H]1C(=O)O)O
• Canonical SMILES: O[C@@H]1CN[C@@H](C1)C(=O)O
• InChI: InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1
• InChIKey: PMMYEEVYMWASQN-IMJSIDKUSA-N

名称和登记号

名称

• IUPAC标准名: (2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid
• IUPAC传统名: L-hydroxyproline
• 别名: (2S,4S)-(-)-4-羟基-2-吡咯烷羧酸; 顺式-4-羟基-L-脯氨酸; 顺-4-羟基-L-脯氨酸; CHP; cis-4-Hydroxy-L-proline; (2S,4S)-(-)-4-Hydroxy-2-pyrrolidinecarboxylic acid; (4S)-4-Hydroxy-L-proline; (2S,4S)-4-Hydroxyproline; (S)-Allo-hydroxyproline; (2S,4S)-4-Hydroxypyrrolidine-2-carboxylic Acid; L-Allohydroxyproline; cis-4-Hydroxyproline; cis-Hydroxyproline; cis-4-Hydroxy-L-proline; (2S,4S)-(-)-4-Hydroxypyrrolidine-2-carboxylic acid; H-cis-Hyp-OH; (2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid

登记号

• CAS号: 618-27-9
• EC号: 210-542-1
• MDL号: MFCD00064319
• Beilstein号: 81440
• PubChem SID: 162226654; 24880039; 24895470
• PubChem CID: 440015

理论计算性质

• Acid pKa: 1.641382
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): -3.7163465
• LogD (pH = 7.4): -3.7165344
• Log P: -3.7163188
• 摩尔折射率: 29.3822 cm^3
• 极化性: 11.9828205 Å^3
• 极化表面积: 69.56 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Water
• 外观: WHite Solid
• 熔点: <225°C (dec.); 253-257 °C (dec.); 257 °C (dec.)(lit.); ca 250°C dec.
• 比旋光度: [α]20/D -59.0°, c = 2 in H2O; [α]20/D -59±1°, c = 1% in H2O; -59 (c=2 in water)

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere
• 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: ≥99.0% (NT); 97%; 99%
• 级别: puriss.
• Empirical Formula (Hill Notation): C5H9NO3

详细说明

Sigma Aldrich - H1637

Other Notes
Constituent of Amanita sp. peptide toxins but not of animal proteins like collagen.
Application
cis-4-Hydroxy-L-proline (CHP) is a proline analog that inhibits collagen synthesis and has been used as an anticancer compound.1 CHP blocked myotube formation and expression of sarcomeric myosin heavy chain in C2C12 murine skeletal muscle cells.2 CHP inhibited proliferation of murine Panc02 pancreatic carcinoma cell line3 and rat pancreatic carcinoma cell line DSL6A.4

Sigma Aldrich - 56248

Other Notes
Proline antagonist in collagen synthesis. Inhibits human skin fibroblast growth and collagen production in culture1; Specifically inhibits cultured tumour cells that synthesize basement-membrane collagen2,3; Its incorporation inhibits secretion of procollagen4

Toronto Research Chemicals - H952375

Hydroxyprolines are valuable chiral building blocks for organic synthesis of pharmaceuticals. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- a

参考文献

• Lawrence, C., et al.: Biochem. J., 313, 185 (1996)
• Mori, H., et al.: J. Bacteriol., 179, 5677 (1996)
• Clifton, I., et al.: Eur. J. Biochem., 268, 6625 (1996)