ethyl 2-acetamino-2-ethoxycarbonyl-9-(4-imidazolyl)-7-azanonanoate | 88238-59-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-acetamino-2-ethoxycarbonyl-9-(4-imidazolyl)-7-azanonanoate
• 英文别名: diethyl 2-acetamido-2-[4-[2-(1H-imidazol-5-yl)ethylamino]butyl]propanedioate
• CAS: 88238-59-9
• 化学式: C₁₈H₃₀N₄O₅
• 分子量: 382.46
• InChiKey: RKULNTBZOLAZCN-UHFFFAOYSA-N

物化性质

• 沸点：
  600.5±55.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetamino-2-ethoxycarbonyl-9-(4-imidazolyl)-7-azanonanoate 在 盐酸 作用下， 反应 5.0h， 生成 (+/-)-gizzerosine trihydrochloride
  参考文献：
  名称：

  Mori, Kenji; Okazaki, Tomomi; Noguchi, Tadashi, Agricultural and Biological Chemistry, 1983, vol. 47, # 9, p. 2131 - 2132

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-acetamino-6,7-epoxy-2-ethoxycarbonyl-7-methyloctanoate 在 水 、 sodium cyanoborohydride 、 过碘酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 0.17h， 生成 ethyl 2-acetamino-2-ethoxycarbonyl-9-(4-imidazolyl)-7-azanonanoate
  参考文献：
  名称：

  合成的外消旋和旋光形式的鸟嘌呤肌苷，是雏鸡的izz肌侵蚀的诱因

  摘要：

  合成了外消旋体和吡咯烷磺酸[2-氨基-9-（4-咪唑基）-7-氮杂壬酸]的（R）-和（S）-形式，并将（S）-异构体鉴定为有毒物质鱼粉中的这种物质会导致小鸡严重的izz侵蚀（黑呕吐物）。

  DOI：

  10.1016/s0040-4020(01)96782-1

文献信息

• Methods
  申请人：Sattentau James Quentin

  公开号：US20070110759A1

  公开（公告）日：2007-05-17

  The presence of aldehydic groups on proteins and lipoproteins is associated with various pathological conditions such as atherosclerosis, diabetes and alcoholic liver disease. Respiratory syncytial virus (RSV) is a major cause of severe respiratory disease in infants and the elderly. RSV vaccine research has been impeded because a formalin-inactivated vaccine used in the 1960s predisposed infants to enhanced disease following subsequent natural infection. The molecular basis for the vaccine-induced hypersensitivity has not, however, been elucidated. We show here that addition of reactive carbonyl groups to ovalbumin (OVA) by treatment with glycolaldehyde or formaldehyde increases the protein's immunogenicity in mice, and biases the immune response towards a Th2-type response. The increased immunogenicity and the Th2-type response can both be abrogated by reductive elimination of the reactive carbonyl groups. We demonstrate that RSV inactivated by formaldehyde (FI-RSV), following a protocol used previously to prepare the vaccine, contains reactive carbonyl groups. Using a well-established model of FI-RSV vaccine-induced pathology, immunisation of mice with FI-RSV and subsequent challenge of the mice with live RSV induced Th2-type responses, lung eosinophilia and weight loss that were abrogated by reductive elimination of the reactive carbonyl groups. We thus propose that the addition of reactive carbonyl groups to RSV during inactivation is the major mechanism that drives the Th2-immune response and associated pathology. Moreover, we suggest that the addition of reactive carbonyl groups to other antigens, including vaccines, may be responsible for other hypersensitive and allergic reactions described in the literature.
• Mori, Kenji; Okazaki, Tomomi; Noguchi, Tadashi, Agricultural and Biological Chemistry, 1983, vol. 47, # 9, p. 2131 - 2132
  作者：Mori, Kenji、Okazaki, Tomomi、Noguchi, Tadashi、Naito, Hiroshi

  DOI：——

  日期：——
• Synthesis of the racemic and optically active forms of gizzerosine, the inducer of gizzard erosion in chicks
  作者：Kenji Mori、Takeshi Sugai、Yukari Maeda、Tomomi Okazaki、Tadashi Noguchi、Hiroshi Naito

  DOI：10.1016/s0040-4020(01)96782-1

  日期：1985.1

  The racemate and both the (R)- and (S)-forms of gizzerosine [2-amino-9-(4-imidazolyl)-7-azanonanoic acid] were synthesised, and the (S)-isomer was identified as the toxic substance in fish meal causing severe gizzard erosion (black vomit) in chicks.

  合成了外消旋体和吡咯烷磺酸[2-氨基-9-（4-咪唑基）-7-氮杂壬酸]的（R）-和（S）-形式，并将（S）-异构体鉴定为有毒物质鱼粉中的这种物质会导致小鸡严重的izz侵蚀（黑呕吐物）。