[3-((S)-2-Carbamoyl-pyrrolidin-1-yl)-3-oxo-propyl]-carbamic acid tert-butyl ester | 87297-43-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: [3-((S)-2-Carbamoyl-pyrrolidin-1-yl)-3-oxo-propyl]-carbamic acid tert-butyl ester
• 英文别名: N-tert.-butoxycarbonyl-beta-alanyl-L-proline amide；tert-butyl N-[3-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-oxopropyl]carbamate
• CAS: 87297-43-6
• 化学式: C₁₃H₂₃N₃O₄
• 分子量: 285.343
• InChiKey: SXRVTFBLKDHUGH-VIFPVBQESA-N

物化性质

• 沸点：
  538.1±50.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [3-((S)-2-Carbamoyl-pyrrolidin-1-yl)-3-oxo-propyl]-carbamic acid tert-butyl ester 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 (S)-1-(3-Trifluoromethanesulfonylamino-propionyl)-pyrrolidine-2-carboxylic acid amide
  参考文献：
  名称：

  Control of Protein−Protein Interactions:  Structure-Based Discovery of Low Molecular Weight Inhibitors of the Interactions between Pin1 WW Domain and Phosphopeptides

  摘要：

  Interactions involving phosphorylated Ser/Thr-Pro motifs in proteins play a key role in numerous regulatory processes in the cell. Here, we investigate potential ligands of the WW binding domain of Pin1 in order to inhibit protein-protein interactions between Pin1 and phosphopeptides. Our structure-based strategy implies the synthesis of analogues of the Ac-Thr(PO3H2)-Pro-NH2 dipeptide and relies on high resolution NMR spectroscopy to accurately measure the affinity constants even in the high micromolar range.

  DOI：

  10.1021/jm0500119
• 作为产物：
  描述：

  Boc-beta-丙氨酸 、 L-脯氨酰胺 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 [3-((S)-2-Carbamoyl-pyrrolidin-1-yl)-3-oxo-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Control of Protein−Protein Interactions:  Structure-Based Discovery of Low Molecular Weight Inhibitors of the Interactions between Pin1 WW Domain and Phosphopeptides

  摘要：

  Interactions involving phosphorylated Ser/Thr-Pro motifs in proteins play a key role in numerous regulatory processes in the cell. Here, we investigate potential ligands of the WW binding domain of Pin1 in order to inhibit protein-protein interactions between Pin1 and phosphopeptides. Our structure-based strategy implies the synthesis of analogues of the Ac-Thr(PO3H2)-Pro-NH2 dipeptide and relies on high resolution NMR spectroscopy to accurately measure the affinity constants even in the high micromolar range.

  DOI：

  10.1021/jm0500119

文献信息

• N-Carboxyalkylproline-containing tripeptides
  申请人：SmithKline Beckman Corporation

  公开号：US04456594A1

  公开（公告）日：1984-06-26

  Certain N-carboxyalkyl prolyl-containing tripeptides have been prepared and found to improve kidney function. A species of the group of new compounds is N-(2-carboxyethyl)-L-prolyl-L-alanyl-L-proline which has diuretic activity and increases renal blood flow. The compounds are prepared by chemical reactions which couple an amino acid with a dipeptide.

  某些含有N-羧基烷基脯氨酸三肽的化合物已被制备并发现可改善肾功能。新化合物群中的一种是N-(2-羧乙基)-L-脯氨酰-L-丙氨酸，具有利尿作用并增加肾血流量。这些化合物是通过将氨基酸与二肽偶联的化学反应制备而成。
• N-carboxyalkylproline-containing tripeptides
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0080283A1

  公开（公告）日：1983-06-01

  Certain N-carboxyalkyl prolyl-containing tripeptides have been prepared and found to improve kidney function. A species of the group of new compounds is N-(2-carboxyethyl)-L-prolyl-L-alanyl-L-proline which has diuretic activity and increases renal blood flow. The compounds are prepared by chemical reactions which couple an amino acid with a dipeptide.

  某些含 N-羧烷基脯氨酰的三肽已被制备出来，并被发现能改善肾功能。这组新化合物中的一种是 N-（2-羧乙基）-L-脯氨酰-L-丙氨酰-L-脯氨酸，它具有利尿活性，能增加肾血流量。这些化合物是通过将氨基酸与二肽结合的化学反应制备而成的。
• US4456594A
  申请人：——

  公开号：US4456594A

  公开（公告）日：1984-06-26