(4R,5S,2'R,3'S)-3-(3'-azido-2'-methylhexanoyl)-5-phenyl-4-methyl-2-oxazolidinone | 410087-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,5S,2'R,3'S)-3-(3'-azido-2'-methylhexanoyl)-5-phenyl-4-methyl-2-oxazolidinone
• 英文别名: (4R,5S)-3-[(2R,3S)-3-azido-2-methylhexanoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• CAS: 410087-07-9
• 化学式: C₁₇H₂₂N₄O₃
• 分子量: 330.387
• InChiKey: NEOZKKKJYXELDP-RJZRQDKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5S,2'R,3'S)-3-(3'-azido-2'-methylhexanoyl)-5-phenyl-4-methyl-2-oxazolidinone 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (2R,3S)-3-Azido-2-methyl-hexanoic acid
  参考文献：
  名称：

  Kulokekahilide-1, a Cytotoxic Depsipeptide from the Cephalaspidean Mollusk Philinopsis speciosa

  摘要：

  The cytotoxic depsipeptide kulokekahilide-1, which contains two unusual amino acids, 4-phenylvaline and 3-amino-2-methylhexanoic acid, was isolated from the cephalaspidean mollusk Philinopsis speciosa. Structure elucidation of kulokekahilide-1 was carried out by spectroscopic analysis and chemical degradation. The absolute stereochemistry was determined by Marfey analysis for amino acids and chiral HPLC analysis for hydroxy acids. All four stereoisomers of 4-phenylvaline and 3-amino-2-methylhexanoic acid, which were necessary for Marfey analysis, were synthesized by use of the Heck reaction and Evans's method, respectively. Kulokekahilide-1 showed cytotoxicity against P388 murine leukemia cells with an IC50 value of 2.1 mug/mL.

  DOI：

  10.1021/jo010176z
• 作为产物：
  描述：

  (4R,5S)-3-丙酰基-4-甲基-5-苯基-2-噁唑烷酮 在 吡啶 、 sodium azide 、 15-冠醚-5 、 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 、 lithium bromide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (4R,5S,2'R,3'S)-3-(3'-azido-2'-methylhexanoyl)-5-phenyl-4-methyl-2-oxazolidinone
  参考文献：
  名称：

  Kulokekahilide-1, a Cytotoxic Depsipeptide from the Cephalaspidean Mollusk Philinopsis speciosa

  摘要：

  The cytotoxic depsipeptide kulokekahilide-1, which contains two unusual amino acids, 4-phenylvaline and 3-amino-2-methylhexanoic acid, was isolated from the cephalaspidean mollusk Philinopsis speciosa. Structure elucidation of kulokekahilide-1 was carried out by spectroscopic analysis and chemical degradation. The absolute stereochemistry was determined by Marfey analysis for amino acids and chiral HPLC analysis for hydroxy acids. All four stereoisomers of 4-phenylvaline and 3-amino-2-methylhexanoic acid, which were necessary for Marfey analysis, were synthesized by use of the Heck reaction and Evans's method, respectively. Kulokekahilide-1 showed cytotoxicity against P388 murine leukemia cells with an IC50 value of 2.1 mug/mL.

  DOI：

  10.1021/jo010176z

文献信息

• Kulokekahilide-1, a Cytotoxic Depsipeptide from the Cephalaspidean Mollusk <i>Philinopsis speciosa</i>
  作者：Junji Kimura、Yuuki Takada、Tomoko Inayoshi、Yoichi Nakao、Gilles Goetz、Wesley Y. Yoshida、Paul J. Scheuer

  DOI：10.1021/jo010176z

  日期：2002.3.1

  The cytotoxic depsipeptide kulokekahilide-1, which contains two unusual amino acids, 4-phenylvaline and 3-amino-2-methylhexanoic acid, was isolated from the cephalaspidean mollusk Philinopsis speciosa. Structure elucidation of kulokekahilide-1 was carried out by spectroscopic analysis and chemical degradation. The absolute stereochemistry was determined by Marfey analysis for amino acids and chiral HPLC analysis for hydroxy acids. All four stereoisomers of 4-phenylvaline and 3-amino-2-methylhexanoic acid, which were necessary for Marfey analysis, were synthesized by use of the Heck reaction and Evans's method, respectively. Kulokekahilide-1 showed cytotoxicity against P388 murine leukemia cells with an IC50 value of 2.1 mug/mL.