N-[N¹-(2,4,6-trimethylphenylsulfonyl)carbamimidoyl]-L-proline | 930121-61-2

• 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: N-[N¹-(2,4,6-trimethylphenylsulfonyl)carbamimidoyl]-L-proline
• 英文别名: N-mesitylenesulfonylamidino-L-proline；n-(Mesitylenesulfonylamidino)-l-proline；(2S)-1-[(Z)-N'-(2,4,6-trimethylphenyl)sulfonylcarbamimidoyl]pyrrolidine-2-carboxylic acid
• CAS: 930121-61-2
• 化学式: C₁₅H₂₁N₃O₄S
• 分子量: 339.415
• InChiKey: VANQNABZCPMJMT-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[N¹-(2,4,6-trimethylphenylsulfonyl)carbamimidoyl]-L-proline 在 TEA 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 N-mesitylenesulfonylamidino-L-prolyl-L-alanine
  参考文献：
  名称：

  Derivatives of N-amidinoproline and their use in conventional and solid phase peptide synthesis

  摘要：

  N-Amidinoproline, a hybrid structure modeling key features of the Arg-Pro sequence, was synthesized. The activation of carboxyl group of free N-amidinoproline was found to result in the formation of a cyclic side product, whose structure was confirmed by ESI MS, H-1 NMR, and C-13 NMR spectra. The preparation of N-(mesitylenesulfonylatnidino)-L-proline using the mesitylenesulfonyl derivative of 2-methylisothiourea was demonstrated to be accompanied by partial racemization. The target product was synthesized by modification of N-amidinoproline by mesitylenesulfonyl chloride. The possibility of using N-amidinoproline in the N-terminal modification of a peptide chain was shown by the example of synthesis of an analogue of the 95-98 fragment of fibrinogen alpha chain.

  DOI：

  10.1134/s1068162006060021
• 作为产物：
  描述：

  L-脯氨酸 在 sodium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 26.0h， 生成 N-[N¹-(2,4,6-trimethylphenylsulfonyl)carbamimidoyl]-L-proline
  参考文献：
  名称：

  Derivatives of N-amidinoproline and their use in conventional and solid phase peptide synthesis

  摘要：

  N-Amidinoproline, a hybrid structure modeling key features of the Arg-Pro sequence, was synthesized. The activation of carboxyl group of free N-amidinoproline was found to result in the formation of a cyclic side product, whose structure was confirmed by ESI MS, H-1 NMR, and C-13 NMR spectra. The preparation of N-(mesitylenesulfonylatnidino)-L-proline using the mesitylenesulfonyl derivative of 2-methylisothiourea was demonstrated to be accompanied by partial racemization. The target product was synthesized by modification of N-amidinoproline by mesitylenesulfonyl chloride. The possibility of using N-amidinoproline in the N-terminal modification of a peptide chain was shown by the example of synthesis of an analogue of the 95-98 fragment of fibrinogen alpha chain.

  DOI：

  10.1134/s1068162006060021

文献信息

• Derivatives of N-amidinoproline and their use in conventional and solid phase peptide synthesis
  作者：S. V. Burov、Yu. E. Moskalenko、M. V. Leko、M. Yu. Dorosh、E. F. Panarin

  DOI：10.1134/s1068162006060021

  日期：2006.12

  N-Amidinoproline, a hybrid structure modeling key features of the Arg-Pro sequence, was synthesized. The activation of carboxyl group of free N-amidinoproline was found to result in the formation of a cyclic side product, whose structure was confirmed by ESI MS, H-1 NMR, and C-13 NMR spectra. The preparation of N-(mesitylenesulfonylatnidino)-L-proline using the mesitylenesulfonyl derivative of 2-methylisothiourea was demonstrated to be accompanied by partial racemization. The target product was synthesized by modification of N-amidinoproline by mesitylenesulfonyl chloride. The possibility of using N-amidinoproline in the N-terminal modification of a peptide chain was shown by the example of synthesis of an analogue of the 95-98 fragment of fibrinogen alpha chain.
• Synthesis of N-[N 1-(2,4,6-Trimethylphenylsulfonyl)-carbamimidoyl]-l-proline
  作者：S. V. Burov、Yu. E. Moskalenko、E. F. Panarin

  DOI：10.1134/s1070363206040311

  日期：2006.4