(2S)-2-amino-3-[4-(phosphonooxy)phenyl]propanoic acid

• ChemBase编号: 1729
• 分子式: C9H12NO6P
• 平均质量: 261.168441
• 单一同位素质量: 261.04022374
• SMILES: N[C@@H](Cc1ccc(OP(=O)(O)O)cc1)C(=O)O
• Canonical SMILES: OC(=O)[C@H](Cc1ccc(cc1)OP(=O)(O)O)N
• InChI: InChI=1S/C9H12NO6P/c10-8(9(11)12)5-6-1-3-7(4-2-6)16-17(13,14)15/h1-4,8H,5,10H2,(H,11,12)(H2,13,14,15)/t8-/m0/s1
• InChIKey: DCWXELXMIBXGTH-QMMMGPOBSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-3-[4-(phosphonooxy)phenyl]propanoic acid
• IUPAC传统名: phosphonotyrosine
• 别名: L-3-(4-Hydroxyphenyl)alanine 4’-Phosphate; Phosphotyrosine; O-Phospho-L-tyrosine; L-3-(4-Hydroxyphenyl)alanine 4′-phosphate; L-Tyrosine-O-phosphate; O-Phospho-L-tyrosine; Phosphonotyrosine

登记号

• CAS号: 21820-51-9
• MDL号: MFCD00002603
• Beilstein号: 3150815
• PubChem SID: 160965185; 24899034; 46507690
• PubChem CID: 30819

理论计算性质

JChem

• Acid pKa: 1.3784037
• 质子受体: 6
• 质子供体: 4
• LogD (pH = 5.5): -4.2425585
• LogD (pH = 7.4): -5.104805
• Log P: -1.5143896
• 摩尔折射率: 57.9701 cm^3
• 极化性: 22.964252 Å^3
• 极化表面积: 130.08 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.76
• LOG S: -2.13
• 溶解度: 1.93e+00 g/l

分子性质

理化性质

• 溶解度: Butanol; Water
• 外观: White to Off-White Solid
• 熔点: 226-227°C
• 比旋光度: [α]20/D -5.5±0.5°, c = 1% in 2 M HCl

安全信息

• 保存条件: -20°C Freezer
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C; 2-8°C

产品相关信息

• 纯度: ~95% (sum of enantiomers, HPLC)
• Empirical Formula (Hill Notation): C9H12NO6P

详细说明

DrugBank - DB01962

• Drug Groups: experimental
• Description: An amino acid that occurs in endogenous proteins. Tyrosine phosphorylation and dephosphorylation plays a role in cellular signal transduction and possibly in cell growth control and carcinogenesis. [PubChem]

Sigma Aldrich - 79720

Other Notes
Detection and quantification of phosphotyrosine in proteins1

Toronto Research Chemicals - P365000

Useful in the study of tyrosine-phosphorylation, which has been linked with the malignant transformation of cells by some RNA tumour viruses.

参考文献

• Sefton, B.M., et al.: Cell, 20, 807 (1980)
• Erikson, R., et al.: Perspect. Virol., 11, 93 (1980)
• Lee, E-S, et al.: J. Org. Chem., 59, 2086 (1994)