(S)-2-(2-{2-[((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-methyl]-phenyl}-acetylamino)-3-phenyl-propionic acid methyl ester | 154459-08-2

• 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: (S)-2-(2-{2-[((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-methyl]-phenyl}-acetylamino)-3-phenyl-propionic acid methyl ester
• CAS: 154459-08-2
• 化学式: C₃₀H₃₂N₂O₆
• 分子量: 516.594
• InChiKey: WLVBDNLNQSRURV-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  110.8
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-{2-[((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-methyl]-phenyl}-acetylamino)-3-phenyl-propionic acid methyl ester 在 N-甲基吗啉 、 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 生成 7,10,21,24-tetraaza-31-oxa-2-thia-29,33-dimethyl-9,22-dibenzyl-pentacyclo-(24.3.1.3^{3,5_.14,27_.013,18})-tetratriaconta-1(27),3,5(32),13,15,17,26,29,33-nonaen-8,11,20,23-tetroxid
  参考文献：
  名称：

  Parallel β-sheet conformation in macrocycles

  摘要：

  Amino acids (Val, Phe) are combined with two rigid spacers phenoxathiin-4,6-dicarboxylic acid (5) and 2,8-dimethyl-4,6-bis(aminomethyl)phenoxathiin-10,10-dioxide (6) to synthesize the cyclic structures 1 (5-Val/Val-6) and 2 (5-Phe/Phe-6). The diacid and diamino spacers 5 and 6 provide a distance between the attached short peptides which allows hydrogen bonding similar to that found in a parallel beta-sheet. The beta-sheet conformation of 1 and 2 is proved by NMR measurements at low temperatures. The derived dihedral angles and NOE distances are compared to the most stable conformations of 1 calculated with MM3 and AM1.

  DOI：

  10.1016/s0040-4020(01)80237-4
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 、 1,2-苯二乙酸 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以88%的产率得到(S)-2-(2-{2-[((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-methyl]-phenyl}-acetylamino)-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  Parallel β-sheet conformation in macrocycles

  摘要：

  Amino acids (Val, Phe) are combined with two rigid spacers phenoxathiin-4,6-dicarboxylic acid (5) and 2,8-dimethyl-4,6-bis(aminomethyl)phenoxathiin-10,10-dioxide (6) to synthesize the cyclic structures 1 (5-Val/Val-6) and 2 (5-Phe/Phe-6). The diacid and diamino spacers 5 and 6 provide a distance between the attached short peptides which allows hydrogen bonding similar to that found in a parallel beta-sheet. The beta-sheet conformation of 1 and 2 is proved by NMR measurements at low temperatures. The derived dihedral angles and NOE distances are compared to the most stable conformations of 1 calculated with MM3 and AM1.

  DOI：

  10.1016/s0040-4020(01)80237-4