methyl (2S,3R,4S)-3-ethenyl-4-[[(1S)-7-fluoro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate | 1039124-12-3

• 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: methyl (2S,3R,4S)-3-ethenyl-4-[[(1S)-7-fluoro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• CAS: 1039124-12-3
• 化学式: C₂₇H₃₃FN₂O₉
• 分子量: 548.565
• InChiKey: WUHVKKWIASYDBI-NTXHKPOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  163
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  6-氟色氨酸 、 开联番木鳖苷 在 recombinant strictosidine synthase 作用下， 以 phosphate buffer 为溶剂， 生成 methyl (2S,3R,4S)-3-ethenyl-4-[[(1S)-7-fluoro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
  参考文献：
  名称：

  Substrate specificity of strictosidine synthase

  摘要：

  Strictosidine synthase catalyzes a Pictet-Spengler reaction in the first step in the biosynthesis of terpene indole alkaloids to generate strictosidine. The substrate requirements for strictosidine synthase are systematically and quantitatively examined and the enzymatically generated compounds are processed by the second enzyme in this biosynthetic pathway. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.098

文献信息

• Substrate specificity and diastereoselectivity of strictosidine glucosidase, a key enzyme in monoterpene indole alkaloid biosynthesis
  作者：Nancy Yerkes、Jia Xin Wu、Elizabeth McCoy、M. Carmen Galan、Shi Chen、Sarah E. O’Connor

  DOI：10.1016/j.bmcl.2007.11.063

  日期：2008.5

  intermediate from which thousands of monoterpene indole alkaloids are derived. The steady-state kinetics of SGD with a variety of strictosidine analogs revealed the substrate preferences of this enzyme at two key positions of the strictosidine substrate. Additionally, SGD from C. roseus turns over both strictosidine and its stereoisomer vincoside, indicating that although this enzyme prefers the naturally occurring

  来自长春花的胡豆苷葡萄糖苷酶 (SGD) 催化胡豆苷的去糖基化，胡豆苷是一种中间体，从中衍生出数千种单萜吲哚生物碱。SGD 与各种胡豆苷类似物的稳态动力学揭示了这种酶在胡豆苷底物的两个关键位置的底物偏好。此外，来自 C. roseus 的 SGD 翻转了胡豆苷及其立体异构体长春花苷，这表明虽然这种酶更喜欢天然存在的非对映异构体，但该酶并不完全具有非对映选择性。强调了 SGD 底物特异性在 C. roseus 代谢工程工作中的影响。
• Substrate specificity of strictosidine synthase
  作者：Elizabeth McCoy、M. Carmen Galan、Sarah E. O’Connor

  DOI：10.1016/j.bmcl.2006.01.098

  日期：2006.5

  Strictosidine synthase catalyzes a Pictet-Spengler reaction in the first step in the biosynthesis of terpene indole alkaloids to generate strictosidine. The substrate requirements for strictosidine synthase are systematically and quantitatively examined and the enzymatically generated compounds are processed by the second enzyme in this biosynthetic pathway. (C) 2006 Elsevier Ltd. All rights reserved.