1-(3-巯基丙基)-L-脯氨酸 | 80900-82-9

• 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
• 中文名称: 1-(3-巯基丙基)-L-脯氨酸
• 英文名称: 1-(3-mercaptopropyl)-L-proline
• 英文别名: N-(3-mercaptopropyl)-proline；N-(3-Mercaptopropyl)-prolin；(3-Mercaptopropyl)-prolin；(2S)-1-(3-sulfanylpropyl)pyrrolidine-2-carboxylic acid
• CAS: 80900-82-9
• 化学式: C₈H₁₅NO₂S
• 分子量: 189.279
• InChiKey: XQKGVZRVPCZRIC-ZETCQYMHSA-N

物化性质

• 沸点：
  337.9±37.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-巯基丙基)-L-脯氨酸 、 L-焦谷氨酸 在 硫酸 作用下， 以 苯 为溶剂， 反应 18.0h， 以73%的产率得到L-焦谷氨酸甲酯
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors: importance of the amide carbonyl of mercaptoacyl amino acids for hydrogen bonding to the enzyme

  摘要：

  A series of mercaptoacyl amino acids and related compounds was synthesized and evaluated for inhibition of angiotensin-converting enzyme (ACE) in order to determine the nature and importance of the putative interaction between ACE and the amide moiety of inhibitors such as captopril (3-mercapto-2-methylpropanoyl-L-proline). It was concluded that the interaction involves a hydrogen bond from a donor site on ACE to the oxygen of the amide carbonyl. Compounds in which the amide moiety is replaced by other groups (ester, ketone, sulfonamide) capable of accepting a hydrogen bond are effective inhibitors, but compounds in which only the geometrical features of the amide are retained are ineffective inhibitors. The presence of an NH group is not necessary for effective inhibition. The activity of a series of mercaptoacyl cycloalkyl carboxylic acids parallels the activity of the isosteric series of mercaptoacyl imino acids.

  DOI：

  10.1021/jm00345a011
• 作为产物：
  描述：

  L-脯氨酸叔丁酯 在 ammonium hydroxide 、 sodium hydride 、 三氟乙酸 作用下， 以 various solvent(s) 为溶剂， 反应 5.0h， 生成 1-(3-巯基丙基)-L-脯氨酸
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors: importance of the amide carbonyl of mercaptoacyl amino acids for hydrogen bonding to the enzyme

  摘要：

  A series of mercaptoacyl amino acids and related compounds was synthesized and evaluated for inhibition of angiotensin-converting enzyme (ACE) in order to determine the nature and importance of the putative interaction between ACE and the amide moiety of inhibitors such as captopril (3-mercapto-2-methylpropanoyl-L-proline). It was concluded that the interaction involves a hydrogen bond from a donor site on ACE to the oxygen of the amide carbonyl. Compounds in which the amide moiety is replaced by other groups (ester, ketone, sulfonamide) capable of accepting a hydrogen bond are effective inhibitors, but compounds in which only the geometrical features of the amide are retained are ineffective inhibitors. The presence of an NH group is not necessary for effective inhibition. The activity of a series of mercaptoacyl cycloalkyl carboxylic acids parallels the activity of the isosteric series of mercaptoacyl imino acids.

  DOI：

  10.1021/jm00345a011

文献信息

• [DE] VERFAHREN ZUR HERSTELLUNG VON AMIDINEN<br/>[EN] PROCESS FOR PREPARING AMIDINES<br/>[FR] PROCEDE DE PRODUCTION D'AMIDINES
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：WO1998009950A1

  公开（公告）日：1998-03-12

  (DE) Es wird ein Verfahren zur Herstellung von Amidinen und deren Salzen mit anorganischen oder organischen Säuren beschrieben, welches darin besteht, daß man das entsprechende Nitril in Gegenwart einer Mercaptocarbonsäure und gegebenenfalls in Gegenwart eines anorganischen oder organischen Ammoniumsalzes mit Ammoniak, einem C1-C6-Alkylamin oder Hydrazin umsetzt.(EN) The invention concerns a process for preparing amidines and their salts with inorganic or organic acids. According to this process, the corresponding nitrile is reacted with ammonia, a C1-C6 alkylamine or hydrazine in the presence of a mercapto carboxylic acid and optionally in the presence of an inorganic or organic ammonium salt.(FR) L'invention concerne un procédé de production d'amidines et leurs sels avec des acides inorganiques et organiques. Ledit procédé consiste à faire réagir le nitrile approprié en présence d'un acide mercaptocarboxylique et le cas échéant en présence d'un sel d'ammonium inorganique ou organique, avec de l'ammoniac, une alkylamine C1-C6 ou de l'hydrazine.

  该发明涉及一种使用无机或有机酸制备 amidines 及其盐的方法。根据这种方法，在 mercaptoboric 酸的存在下，将相应的 nitrile 与 NH3、C1-C6 酮胺或 hydrazine 反应，并且在必要时可以在无机或有机的 ammonium 盐存在的条件下进行。
• VERFAHREN ZUR HERSTELLUNG VON AMIDINEN
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0931069A1

  公开（公告）日：1999-07-28
• US6204385B1
  申请人：——

  公开号：US6204385B1

  公开（公告）日：2001-03-20
• Angiotensin-converting enzyme inhibitors: importance of the amide carbonyl of mercaptoacyl amino acids for hydrogen bonding to the enzyme
  作者：Michael E. Condon、Edward W. Petrillo、Denis E. Ryono、Joyce A. Reid、Richard Neubeck、Mohindar Puar、James E. Heikes、Emily F. Sabo、Kathryn A. Losee

  DOI：10.1021/jm00345a011

  日期：1982.3

  A series of mercaptoacyl amino acids and related compounds was synthesized and evaluated for inhibition of angiotensin-converting enzyme (ACE) in order to determine the nature and importance of the putative interaction between ACE and the amide moiety of inhibitors such as captopril (3-mercapto-2-methylpropanoyl-L-proline). It was concluded that the interaction involves a hydrogen bond from a donor site on ACE to the oxygen of the amide carbonyl. Compounds in which the amide moiety is replaced by other groups (ester, ketone, sulfonamide) capable of accepting a hydrogen bond are effective inhibitors, but compounds in which only the geometrical features of the amide are retained are ineffective inhibitors. The presence of an NH group is not necessary for effective inhibition. The activity of a series of mercaptoacyl cycloalkyl carboxylic acids parallels the activity of the isosteric series of mercaptoacyl imino acids.