Ethyl-bromacetimidat | 72201-38-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: Ethyl-bromacetimidat
• 英文别名: Ethyl bromoacetimidate；ethyl 2-bromoethanimidate
• CAS: 72201-38-8
• 化学式: C₄H₈BrNO
• 分子量: 166.018
• InChiKey: UHRNNTJUJLITEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ethyl-bromacetimidat 、 聚甘氨酸 生成 Bromacetamidinoessigsaeure
  参考文献：
  名称：

  Ethyl Bromoacetimidate, a NH₂-Specific Heterobifunctional Reagent Model Reactions with Ribonuclease

  摘要：

  Ethyl bromoacetimidate was designed as a potential reagent for cross-linking protein NH2 groups with a vicinal nucleophile. The chemical properties of this compound were studied by model reactions with small molecules. Ethyl bromoacetimidate amidinates lysine residues in ribonuclease at pH 9. In a second step, at lower pH values, one of the bromoacetamidino groups bound to the enzyme alkylates a proximal histidine residue. This substitution is pH-dependent with a sharp optimum at 5.6, the same as was earlier observed for alkylation of histidine-119: histidine-12 by halogenoacetates and halogenoacetamides. A common mechanism is suggested for all these types of alkylation. Ethyl bromoacetimidate thus appears as a short-distance crosslinker which can be used, for example, to explore chemically the microenvironment of an essential lysine residue of an enzyme within the active site.

  DOI：

  10.1515/bchm2.1979.360.2.1257

文献信息

• AVI A. I.; REMLI M.; CONDOM R.; GUEDJ R., J. FLUOR. CHEM., 1981, 17, NO 6, 565-580
  作者：AVI A. I.、 REMLI M.、 CONDOM R.、 GUEDJ R.

  DOI：——

  日期：——
• Ethyl Bromoacetimidate, a NH₂-Specific Heterobifunctional Reagent Model Reactions with Ribonuclease
  作者：Jacques DIOPOH、Martin OLOMUCKI

  DOI：10.1515/bchm2.1979.360.2.1257

  日期：1979.1

  Ethyl bromoacetimidate was designed as a potential reagent for cross-linking protein NH2 groups with a vicinal nucleophile. The chemical properties of this compound were studied by model reactions with small molecules. Ethyl bromoacetimidate amidinates lysine residues in ribonuclease at pH 9. In a second step, at lower pH values, one of the bromoacetamidino groups bound to the enzyme alkylates a proximal histidine residue. This substitution is pH-dependent with a sharp optimum at 5.6, the same as was earlier observed for alkylation of histidine-119: histidine-12 by halogenoacetates and halogenoacetamides. A common mechanism is suggested for all these types of alkylation. Ethyl bromoacetimidate thus appears as a short-distance crosslinker which can be used, for example, to explore chemically the microenvironment of an essential lysine residue of an enzyme within the active site.