cyclo[OOrn-N(Me)Tyr-OVal-N(Me)Val-OVal-D-N(Me)Trp] | 185448-55-9

• 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: cyclo[OOrn-N(Me)Tyr-OVal-N(Me)Val-OVal-D-N(Me)Trp]
• 英文别名: (3S,6S,9R,12S,15S,18S)-6-(3-aminopropyl)-3-[(4-hydroxyphenyl)methyl]-9-(1H-indol-3-ylmethyl)-4,10,16-trimethyl-12,15,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
• CAS: 185448-55-9
• 化学式: C₄₃H₅₉N₅O₁₀
• 分子量: 805.969
• InChiKey: AAFFAGZCNVFYEP-PQVJJDQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  58
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  202
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  氨基亚氨基甲烷磺酸 、 cyclo[OOrn-N(Me)Tyr-OVal-N(Me)Val-OVal-D-N(Me)Trp] 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以73%的产率得到cyclo[OArg-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：

  L-α-羟基异戊酸 在 palladium dihydroxide 盐酸 、 4-二甲氨基吡啶 、 异丙烯基氯甲酸酯 、 四丁基氟化铵 、 氢气 、 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 、 吡啶 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 165.42h， 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