(2S,3S)-2-[[2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[(2E,5S,6S,7S,8E)-7-[(2R)-2-aminopropanoyl]oxy-2,6,8-trimethyl-5-(methylsulfanylmethoxy)deca-2,8-dienoyl]oxy-4-methylpentanoyl]amino]propanoyl]-methylamino]-3-phenylpropanoyl]-methylamino]acetyl]amino]-3-methylpentanoic acid | 1075710-30-3

• 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: (2S,3S)-2-[[2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[(2E,5S,6S,7S,8E)-7-[(2R)-2-aminopropanoyl]oxy-2,6,8-trimethyl-5-(methylsulfanylmethoxy)deca-2,8-dienoyl]oxy-4-methylpentanoyl]amino]propanoyl]-methylamino]-3-phenylpropanoyl]-methylamino]acetyl]amino]-3-methylpentanoic acid
• CAS: 1075710-30-3
• 化学式: C₄₆H₇₃N₅O₁₁S
• 分子量: 904.179
• InChiKey: QRAJRYROGHSZEA-QQBRUPPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  63
• 可旋转键数：
  29
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  249
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-[[2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[(2E,5S,6S,7S,8E)-7-[(2R)-2-aminopropanoyl]oxy-2,6,8-trimethyl-5-(methylsulfanylmethoxy)deca-2,8-dienoyl]oxy-4-methylpentanoyl]amino]propanoyl]-methylamino]-3-phenylpropanoyl]-methylamino]acetyl]amino]-3-methylpentanoic acid 在 2,6-二甲基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 水 、 silver nitrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 kulokekahilide-2
  参考文献：
  名称：

  The total synthesis and structure–activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs

  摘要：

  We successfully completed the total synthesis of kulokekahilide-2, a cytotoxic depsipeptide from the Cephalaspiedean mollusk Phillinopsis speciosa. We have revised the absolute stereochemistry of kulokekahilide-2 to 21-L-Ala, 24-D-MePhe, 37-L-Ile, 43-D-Ala, 15-D-Hica, and 5S,6S,7S-Dtda. We also investigated the cause of the mis-assignment of the configuration in the originally proposed kulokekahilide-2 and concluded that methanolysis using MeONa caused partial racemization, which led to the mis-assignment. The structure activity relationships of kulokekahilide-2 and its analogs indicate the importance of an L-amino acid at position 21. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.094
• 作为产物：
  描述：

  (R)-2-羟基-4-甲基戊酸 在 吡啶 、 4-二甲氨基吡啶 、 ammonium acetate 、 1-羟基苯并三唑 、 氟化氢吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 二乙胺 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 83.5h， 生成 (2S,3S)-2-[[2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[(2E,5S,6S,7S,8E)-7-[(2R)-2-aminopropanoyl]oxy-2,6,8-trimethyl-5-(methylsulfanylmethoxy)deca-2,8-dienoyl]oxy-4-methylpentanoyl]amino]propanoyl]-methylamino]-3-phenylpropanoyl]-methylamino]acetyl]amino]-3-methylpentanoic acid
  参考文献：
  名称：

  The total synthesis and structure–activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs

  摘要：

  We successfully completed the total synthesis of kulokekahilide-2, a cytotoxic depsipeptide from the Cephalaspiedean mollusk Phillinopsis speciosa. We have revised the absolute stereochemistry of kulokekahilide-2 to 21-L-Ala, 24-D-MePhe, 37-L-Ile, 43-D-Ala, 15-D-Hica, and 5S,6S,7S-Dtda. We also investigated the cause of the mis-assignment of the configuration in the originally proposed kulokekahilide-2 and concluded that methanolysis using MeONa caused partial racemization, which led to the mis-assignment. The structure activity relationships of kulokekahilide-2 and its analogs indicate the importance of an L-amino acid at position 21. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.094

文献信息

• The total synthesis and structure–activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs
  作者：Yuuki Takada、Masahiro Umehara、Ryosuke Katsumata、Yoichi Nakao、Junji Kimura

  DOI：10.1016/j.tet.2011.10.094

  日期：2012.1

  We successfully completed the total synthesis of kulokekahilide-2, a cytotoxic depsipeptide from the Cephalaspiedean mollusk Phillinopsis speciosa. We have revised the absolute stereochemistry of kulokekahilide-2 to 21-L-Ala, 24-D-MePhe, 37-L-Ile, 43-D-Ala, 15-D-Hica, and 5S,6S,7S-Dtda. We also investigated the cause of the mis-assignment of the configuration in the originally proposed kulokekahilide-2 and concluded that methanolysis using MeONa caused partial racemization, which led to the mis-assignment. The structure activity relationships of kulokekahilide-2 and its analogs indicate the importance of an L-amino acid at position 21. (C) 2011 Elsevier Ltd. All rights reserved.