3-(1-Ethyl-2,5-dioxopyrrolidin-3-yl)sulfanylpropanoic acid | 1154618-29-7

• 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: 3-(1-Ethyl-2,5-dioxopyrrolidin-3-yl)sulfanylpropanoic acid
• CAS: 1154618-29-7
• 化学式: C₉H₁₃NO₄S
• 分子量: 231.273
• InChiKey: WPBJMZWRSTWGSI-UHFFFAOYSA-N

物化性质

• 沸点：
  467.9±40.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-乙基马来酰亚胺 、 3-巯基丙酸 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以90%的产率得到3-(1-Ethyl-2,5-dioxopyrrolidin-3-yl)sulfanylpropanoic acid
  参考文献：
  名称：

  Tunable Degradation of Maleimide–Thiol Adducts in Reducing Environments

  摘要：

  Addition chemistries are widely used in preparing biological conjugates, and in particular, maleimide-thiol adducts have been widely employed. Here, we show that the resulting succinimide thioether formed by the Michael-type addition of thiols to N-ethylmaleimide (NEM), generally accepted as stable, undergoes retro and exchange reactions in the presence of other thiol compounds at physiological pH and temperature, offering a novel strategy for controlled release. Model studies (H-1 NMR, HPLC) of NEM conjugated to 4-mercaptophenylcetic acid (MPA), N-acetylcysteine, or 3-mercaptopropionic acid (MP) incubated with glutathione showed half-lives of conversion from 20 to 80 h, with extents of conversion from 20% to 90% for MPA and N-acetylcysteine conjugates. After ring-opening, the resultant succinimide thioether did not show retro and exchange reactions.The kinetics of the retro reactions and extent of exchange can be modulated by the Michael donor's reactivity; therefore, the degradation of maleimide-thiol adducts could be tuned for controlled release of drugs or degradation of materials at time scales different than those currently possible via disulfide-mediated release. Such approaches may find a new niche for controlled release in reducing environments relevant in chemotherapy and subecullar trafficking.

  DOI：

  10.1021/bc200148v

文献信息

• Method for preparing crosslinked polyelectrolyte multilayer films
  申请人：Picart Catherine

  公开号：US20070129792A1

  公开（公告）日：2007-06-07

  The invention relates to methods for preparing crosslinked polyelectrolytes, in particular crosslinked polyelectrolytes multilayer films. The invention also relates to a method of coating a surface, and the obtained coated article.
• METHOD FOR PREPARING CROSSLINKED POLYELECTROLYTE MULTILAYER FILMS
  申请人：Picart Catherine

  公开号：US20140328883A1

  公开（公告）日：2014-11-06

  The invention relates to methods for preparing crosslinked polyelectrolytes, in particular crosslinked polyelectrolytes multilayer films. The invention also relates to a method of coating a surface, and the obtained coated article.
• Tunable Degradation of Maleimide–Thiol Adducts in Reducing Environments
  作者：Aaron D. Baldwin、Kristi L. Kiick

  DOI：10.1021/bc200148v

  日期：2011.10.19

  Addition chemistries are widely used in preparing biological conjugates, and in particular, maleimide-thiol adducts have been widely employed. Here, we show that the resulting succinimide thioether formed by the Michael-type addition of thiols to N-ethylmaleimide (NEM), generally accepted as stable, undergoes retro and exchange reactions in the presence of other thiol compounds at physiological pH and temperature, offering a novel strategy for controlled release. Model studies (H-1 NMR, HPLC) of NEM conjugated to 4-mercaptophenylcetic acid (MPA), N-acetylcysteine, or 3-mercaptopropionic acid (MP) incubated with glutathione showed half-lives of conversion from 20 to 80 h, with extents of conversion from 20% to 90% for MPA and N-acetylcysteine conjugates. After ring-opening, the resultant succinimide thioether did not show retro and exchange reactions.The kinetics of the retro reactions and extent of exchange can be modulated by the Michael donor's reactivity; therefore, the degradation of maleimide-thiol adducts could be tuned for controlled release of drugs or degradation of materials at time scales different than those currently possible via disulfide-mediated release. Such approaches may find a new niche for controlled release in reducing environments relevant in chemotherapy and subecullar trafficking.