(15S,16R)-15-hydroxy-17-methylsulfenyl-ent-atisan-19-oic acid | 474642-86-9

• 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: (15S,16R)-15-hydroxy-17-methylsulfenyl-ent-atisan-19-oic acid
• 英文别名: ent-(15R,16S)-15-hydroxy-17-methylsulfenylatisan-19-oic acid；ent-15α-hydroxy-17-methylthio-16β-atisane-19-oic acid；(1S,4S,5R,9S,10S,12S,13R,14S)-14-hydroxy-5,9-dimethyl-13-(methylsulfanylmethyl)tetracyclo[10.2.2.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 474642-86-9
• 化学式: C₂₁H₃₄O₃S
• 分子量: 366.565
• InChiKey: JPRWRUXEJUBWJD-VYBRGMNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (15S,16R)-15-hydroxy-17-methylsulfenyl-ent-atisan-19-oic acid 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以67%的产率得到(1S,4S,5R,9S,10S,12S,13R,14S)-14-hydroxy-5,9-dimethyl-13-(methylsulfinylmethyl)tetracyclo[10.2.2.01,10.04,9]hexadecane-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and neuroprotective effects of serofendic acid analogues

  摘要：

  Analogues of serofendic acid were prepared and their protective effects against L-glutamate (Glu)-induced neurotoxicity were examined using primary cultures of rat cortical neurons. Some analogues exhibited similar neuroprotective activity to that of serofendic acid.

  DOI：

  10.1016/j.bmcl.2006.07.038
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 六甲基磷酰三胺 、 乙腈 为溶剂， 反应 60.0h， 生成 (15S,16R)-15-hydroxy-17-methylsulfenyl-ent-atisan-19-oic acid
  参考文献：
  名称：

  Synthesis and neuroprotective effects of serofendic acid analogues

  摘要：

  Analogues of serofendic acid were prepared and their protective effects against L-glutamate (Glu)-induced neurotoxicity were examined using primary cultures of rat cortical neurons. Some analogues exhibited similar neuroprotective activity to that of serofendic acid.

  DOI：

  10.1016/j.bmcl.2006.07.038

文献信息

• Stereoselective semi-synthesis of the neuroprotective natural product, serofendic acid
  作者：Dimitri Perusse、Michael J. Smanski

  DOI：10.1039/c9md00145j

  日期：——

  Our synthesis of neuroprotectant serofendic acid from biosourced ent-atis-16-en-19-oic acid represents the best route to date.

  我们从生物来源的ent-atis-16-en-19-oic酸中合成神经保护剂serofendic acid的方法是迄今为止最好的路线。
• Recombinant cells and methods for biosynthesis of ent-atiserenoic acid
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：US10633680B2

  公开（公告）日：2020-04-28

  This disclosure describes recombinant cells and methods for microbial biosynthesis of ent-atiserenoic acid. Thus, in one aspect, this disclosure describes a recombinant cell genetically modified to exhibit increased biosynthesis of ent-atiserenoic acid compared to a comparable control cell. In some cases, the recombinant cell can include a host cell modified to include at least one heterologous polynucleotide encoding at least one enzyme in a biosynthetic pathway that produces ent-atiserenoic acid. In some cases, the recombinant cell can include a host cell and at least one heterologous enzyme in a biosynthetic pathway that produces ent-atiserenoic acid.

  本公开描述了用于ent-atiserenoic acid 微生物生物合成的重组细胞和方法。因此，在一个方面，本公开描述了一种经过基因修饰的重组细胞，与可比对照细胞相比，该细胞的ent-atiserenoic acid 生物合成能力增强。在某些情况下，重组细胞可包括经修饰的宿主细胞，该宿主细胞包括至少一种异源多核苷酸，该多核苷酸编码产生ent-atiserenoic acid的生物合成途径中的至少一种酶。在某些情况下，重组细胞可包括宿主细胞和产生ent-atiserenoic acid的生物合成途径中的至少一种异源酶。
• US7211589B2
  申请人：——

  公开号：US7211589B2

  公开（公告）日：2007-05-01