N-trans-retinoylserine | 868657-02-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-trans-retinoylserine
• 英文别名: (2S)-2-[[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]amino]-3-hydroxypropanoic acid
• CAS: 868657-02-7
• 化学式: C₂₃H₃₃NO₄
• 分子量: 387.519
• InChiKey: LMAARKZBQFFVIV-OFRYMSBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  维A酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 2,2,2-三氟乙醇 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 N-trans-retinoylserine
  参考文献：
  名称：

  Retinoylserine and Retinoylalanine, Natural Products of the Moth Trichoplusia ni

  摘要：

  Insect cells convert vitamin A into a number of retinoids that are evolutionarily conserved with those of mammalian cells. However, insect cells also produce additional natural retinoids. Namely, two retinoic acid peptides, N-trans-retinoylserine (1) and N-trans-retinoylalanine (2), have been isolated from a cell line of the common cabbage looper, Trichoplusia ni. These are the first examples of naturally occurring retinoic acid linked to amino acids through an amide bond; the amino acid moieties are depicted in the more common L-configuration, although the absolute configuration was not determined due to the minuscule sample amount.

  DOI：

  10.1021/np0496791

文献信息

• Retinoylserine and Retinoylalanine, Natural Products of the Moth <i>Trichoplusia </i><i>n</i><i>i</i>
  作者：Barbara Rogge、Yasuhiro Itagaki、Nathan Fishkin、Ester Levi、Ralph Rühl、San-San Yi、Koji Nakanishi、Ulrich Hammerling

  DOI：10.1021/np0496791

  日期：2005.10.1

  Insect cells convert vitamin A into a number of retinoids that are evolutionarily conserved with those of mammalian cells. However, insect cells also produce additional natural retinoids. Namely, two retinoic acid peptides, N-trans-retinoylserine (1) and N-trans-retinoylalanine (2), have been isolated from a cell line of the common cabbage looper, Trichoplusia ni. These are the first examples of naturally occurring retinoic acid linked to amino acids through an amide bond; the amino acid moieties are depicted in the more common L-configuration, although the absolute configuration was not determined due to the minuscule sample amount.