L-N,N,N-trimethylhomoserine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: L-N,N,N-trimethylhomoserine
• 英文别名: N,N,N-trimethyl homoserine；(L)-homoserine betaine；(2S)-4-hydroxy-2-(trimethylazaniumyl)butanoate
• 化学式: C₇H₁₅NO₃
• 分子量: 161.201
• InChiKey: ILXTZIAPBIBHND-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-N,N,N-trimethylhomoserine 在 盐酸 作用下， 反应 15.0h， 以100%的产率得到
  参考文献：
  名称：

  紫嘌呤A，nakirodin A和MDN-0104的合成：构型分配中的隐秘难题和出错风险

  摘要：

  通过合成证明了先前分配给紫癜素A和那奇罗定A的异常（R）构型（貌似毫无疑问）。首次提供了分配给无盐那奇罗汀A的结构的旋光度和NMR数据。通过MDN-0104举例说明了远程立体中心的非对映异构体配置分配中的困难和潜在的错误风险。但是，比较精细的13 C NMR偏差仍可为此类问题提供解决方案。

  DOI：

  10.1016/j.tet.2017.01.029
• 作为产物：
  描述：

  L-高丝氨酸 、 碘甲烷 在 potassium hydrogencarbonate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以85%的产率得到L-N,N,N-trimethylhomoserine
  参考文献：
  名称：

  Bromotyrosine-derived metabolites from the spongeAiolochroia crassa

  摘要：

  A chemical investigation of secondary metabolites from the sponge Aiolochroia crassa has been performed and five bromotyrosine derivatives (1-5) were identified. Their structures have been assigned on the basis of spectroscopic analysis, of which araplysillin III (2) and hexadellin C (3) possess new structures. The absolute configurations of dibromotyrosine moieties of 2 were determined by HPLC analysis of derivatized constituent amino acids obtained from acid hydrolysis. The stereochemistry of the spirocyclohexadienylisoxazoline moiety of compounds 1-3 was deduced from spectroscopic comparison of the same moiety of aerothionin, of which the absolute configuration was previously assigned by X-ray and CD analysis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00553-0

文献信息

• Novel bioactive lipids enhanced HDL-mediated cholesterol efflux from macrophages through the ABCA1 receptor pathway
  作者：Ali Khattib、Manar Shmet、Rasha Ashkar、Tony Hayek、Soliman Khatib

  DOI：10.1016/j.chemphyslip.2023.105367

  日期：2024.1
• Bromotyrosine-derived metabolites from the spongeAiolochroia crassa
  作者：Hongfeng Gao、Michelle Kelly、Mark T. Hamann

  DOI：10.1016/s0040-4020(99)00553-0

  日期：1999.8

  A chemical investigation of secondary metabolites from the sponge Aiolochroia crassa has been performed and five bromotyrosine derivatives (1-5) were identified. Their structures have been assigned on the basis of spectroscopic analysis, of which araplysillin III (2) and hexadellin C (3) possess new structures. The absolute configurations of dibromotyrosine moieties of 2 were determined by HPLC analysis of derivatized constituent amino acids obtained from acid hydrolysis. The stereochemistry of the spirocyclohexadienylisoxazoline moiety of compounds 1-3 was deduced from spectroscopic comparison of the same moiety of aerothionin, of which the absolute configuration was previously assigned by X-ray and CD analysis. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of purpuroine A, nakirodin A and MDN-0104: The hidden puzzles and risk of error in their configurational assignments
  作者：Wen-Ju Wu、Yikang Wu、Bo Liu

  DOI：10.1016/j.tet.2017.01.029

  日期：2017.3

  The unusual (R) configuration previously assigned (with seemingly undoubted evidence) to purpuroin A and nakirodin A was disproved by synthesis. The optical rotation and NMR data for structure assigned for salt-free nakirodin A were made available for the first time. The difficulty and potential risk of error in configurational assignments of diastereomers for remote stereocenters were exemplified

  通过合成证明了先前分配给紫癜素A和那奇罗定A的异常（R）构型（貌似毫无疑问）。首次提供了分配给无盐那奇罗汀A的结构的旋光度和NMR数据。通过MDN-0104举例说明了远程立体中心的非对映异构体配置分配中的困难和潜在的错误风险。但是，比较精细的13 C NMR偏差仍可为此类问题提供解决方案。