Boc-N(Me)Tyr(Bn)-OVal-N(Me)Val-OVal-D-N(Me)Trp-OOrn(Cbz)(Cbz)-OH | 185448-58-2

• 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: Boc-N(Me)Tyr(Bn)-OVal-N(Me)Val-OVal-D-N(Me)Trp-OOrn(Cbz)(Cbz)-OH
• 英文别名: (2S)-2-[(2R)-3-(1H-indol-3-yl)-2-[methyl-[(2S)-3-methyl-2-[(2S)-3-methyl-2-[methyl-[(2S)-3-methyl-2-[(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-(4-phenylmethoxyphenyl)propanoyl]oxybutanoyl]amino]butanoyl]oxybutanoyl]amino]propanoyl]oxy-5-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 185448-58-2
• 化学式: C₆₃H₈₁N₅O₁₅
• 分子量: 1148.36
• InChiKey: MGWFSZAGEMCALK-HHJJVVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  83
• 可旋转键数：
  34
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  250
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Boc-N(Me)Tyr(Bn)-OVal-N(Me)Val-OVal-D-N(Me)Trp-OOrn(Cbz)(Cbz)-OH 在 palladium dihydroxide 盐酸 、 氢气 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 97.17h， 生成 cyclo[OOrn-N(Me)Tyr-OVal-N(Me)Val-OVal-D-N(Me)Trp]
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of a Depsipeptide Mimic of Tendamistat

  摘要：

  The cyclic hexadepsipeptide framework of enniatin B was identified as a template matching the beta-turn tripeptide of tendamistat. The modified analog 1 was synthesized as a tendamistat mimic and compared to the acyclic derivative 2 and the tripeptide Ac-Try-Arg-Tyr-OMe. These compounds were assembled from the dimeric esters 3-5. As an inhibitor of alpha-amylase, 1 is twice as potent as 2 and comparable to the tripeptide. NMR studies of 1 reveal four conformers in equilibrium in a 50:25:15:10 ratio; the ring conformation of the major component is similar to that of the enniatin B template, with the cis geometry of the alpha-hydroxyisovaleryl-N-methylvaline amide linkage; the other conformers differ in the position or presence of the cis amide linkage.

  DOI：

  10.1021/jo9616062
• 作为产物：
  描述：

  2-trimethylsilylethyl (2S)-2-hydroxy-5-(phenylmethoxycarbonylamino)pentanoate 在 盐酸 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 silica gel 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.58h， 生成 Boc-N(Me)Tyr(Bn)-OVal-N(Me)Val-OVal-D-N(Me)Trp-OOrn(Cbz)(Cbz)-OH
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of a Depsipeptide Mimic of Tendamistat

  摘要：

  The cyclic hexadepsipeptide framework of enniatin B was identified as a template matching the beta-turn tripeptide of tendamistat. The modified analog 1 was synthesized as a tendamistat mimic and compared to the acyclic derivative 2 and the tripeptide Ac-Try-Arg-Tyr-OMe. These compounds were assembled from the dimeric esters 3-5. As an inhibitor of alpha-amylase, 1 is twice as potent as 2 and comparable to the tripeptide. NMR studies of 1 reveal four conformers in equilibrium in a 50:25:15:10 ratio; the ring conformation of the major component is similar to that of the enniatin B template, with the cis geometry of the alpha-hydroxyisovaleryl-N-methylvaline amide linkage; the other conformers differ in the position or presence of the cis amide linkage.

  DOI：

  10.1021/jo9616062