(2R,3S,4E)-2-azido-octadec-4-ene-1,3-diol | 130511-47-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2R,3S,4E)-2-azido-octadec-4-ene-1,3-diol
• 英文别名: (2R,3S,4E)-2-azido-4-octadecene-1,3-diol；(2R,3S,4E)-2-azidooctadec-4-ene-1,3-diol；(2R,3S,4E)-2-azido-4-octadecen-1,3-diol；(E,2R,3S)-2-azidooctadec-4-ene-1,3-diol
• CAS: 130511-47-6
• 化学式: C₁₈H₃₅N₃O₂
• 分子量: 325.495
• InChiKey: XAPVDQFHDYWVTA-MCXRAWCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  54.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4E)-2-azido-octadec-4-ene-1,3-diol 在 sodium hydroxide 、 三甲基膦 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到L-赤式-鞘氨醇
  参考文献：
  名称：

  非天然鞘氨醇和精神神经对映体的简明合成。

  摘要：

  精神病药物（半乳糖基鞘氨醇）的积累与克拉伯病的发病机制有关，但是，其细胞毒性的确切机制仍不清楚。在本文中，我们描述了赤藓红神经鞘氨醇，精神神经碱及其相关衍生物的非天然对映异构体的合成，其可以通过机械方式阐明精神神经氨酸的毒性。

  DOI：

  10.1002/ejoc.201000024
• 作为产物：
  描述：

  L-赤式-鞘氨醇 在 4-二甲氨基吡啶 、 triflic azide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以46%的产率得到(2R,3S,4E)-2-azido-octadec-4-ene-1,3-diol
  参考文献：
  名称：

  Synthesis of fluorescent lactosylceramide stereoisomers

  摘要：

  The intracellular distribution of synthetic glycosphingolipids (GSLs) bearing a fluorophore can be monitored in living cells by fluorescence microscopy. We reported previously that variation in the length of the long-chain base and in the structure of the carbohydrate-containing polar head group of (2S,3R) (or D-erythro-)-beta-lactosylceramide (LacCer) did not alter the mechanism of endocytic uptake from the plasma membrane of various mammalian cell types [Singh, R.D., Puri, V., Valiyaveettil, J.T., Marks, D.L., Bittman, R., Pagano, R.E., 2003. Selective caveolin-l-dependent endocytosis of glycosphingolipids. Mol. Biol. Cell 14, 3254-3265]. To extend our examination of the molecular features in LacCer that are responsible for its uptake by the caveolar-requiring endocytic pathway, we have synthesized the three unnatural stereoisomers [(2R,3R)-, (2S,3S)-, and (2R,3S)] of dipyrromethene difluoride (BODIPY (TM))-LacCer. These analogues will be used to probe the role of stereochemistry in the long-chain base of LacCer in the mechanism of endocytic uptake. (c) 2006 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2006.03.001

文献信息

• An enantio- and stereo-controlled synthesis of<scp>L</scp>-erythro- and<scp>D</scp>-threo-C₁₈-sphingosines via the anomalous version of the katsuki–sharpless asymmetric epoxidation reaction
  作者：Seiichi Takano、Yoshiharu Iwabuchi、Kunio Ogasawara

  DOI：10.1039/c39910000820

  日期：——

  A new enantiocontrolled synthesis of L-erythro- and D-threo-sphingosines has been established starting from (R,R)- and meso-1,2-divinylethylene glycols via the anomalous version of the Katsuki–Sharpless asymmetric epoxidation reaction as the key step.

  通过以Katsuki-Sharpless不对称环氧化反应的异常版本作为关键步骤，从(R,R)-和内消旋-1,2-二乙烯基乙二醇出发，已经建立了L-赤型和D-苏型的神经酰胺的新颖对映选择性合成方法。
• Studies on the inhibition of sphingosine-1-phosphate lyase by stabilized reaction intermediates and stereodefined azido phosphates
  作者：Pol Sanllehí、José-Luís Abad、Jordi Bujons、Josefina Casas、Antonio Delgado

  DOI：10.1016/j.ejmech.2016.08.008

  日期：2016.11

  te lyase have been designed and tested on the bacterial (StS1PL) and the human (hS1PL) enzymes. Amino phosphates 1, 12, and 32, mimicking the intermediate aldimines of the catalytic process, were weak inhibitors on both enzyme sources. On the other hand, a series of stereodefined azido phosphates, resulting from the replacement of the amino group of the natural substrates with an azido group, afforded

  已经设计了两种PLP依赖性酶鞘氨醇-1-磷酸裂解酶抑制剂，并在细菌（StS1PL）和人（hS1PL）酶上进行了测试。氨基磷酸盐1，12，和32，模仿催化过程的中间醛亚胺，分别在两个酶来源弱抑制剂。另一方面，通过用叠氮基团取代天然底物的氨基而产生的一系列立体定义的叠氮基磷酸酯，在两种酶源上均提供了低微摩尔范围内的竞争性抑制剂。这种相似的行为代表了两种酶在其活性位点水平上报道的结构相似性的实验证据。有趣的是，反-非天然对映异构体系列的异构体，是hS1PL上最有效的抑制剂。
• Fujita, Shuji; Sugimoto, Mamoru; Tomita, Kenkichi, Agricultural and Biological Chemistry, 1991, vol. 55, # 10, p. 2561 - 2570
  作者：Fujita, Shuji、Sugimoto, Mamoru、Tomita, Kenkichi、Nakahara, Yoshiaki、Ogawa, Tomoya

  DOI：——

  日期：——
• Concise Synthesis of the Unnatural Sphingosine and Psychosine Enantiomer
  作者：Archana R. Parameswar、Jacqueline A. Hawkins、Laurel K. Mydock、Mark S. Sands、Alexei V. Demchenko

  DOI：10.1002/ejoc.201000024

  日期：2010.6

  accumulation of psychosine (galactosyl sphingosine) has been associated with the pathogenesis of Krabbe disease, however, the exact mechanism of its cytotoxicity remains unclear. Herein, we describe the synthesis of the unnatural enantiomer of erythrosphingosine, psychosine, and related derivatives thereof that would allow for the mechanistic elucidation of the toxicity of psychosine.

  精神病药物（半乳糖基鞘氨醇）的积累与克拉伯病的发病机制有关，但是，其细胞毒性的确切机制仍不清楚。在本文中，我们描述了赤藓红神经鞘氨醇，精神神经碱及其相关衍生物的非天然对映异构体的合成，其可以通过机械方式阐明精神神经氨酸的毒性。
• Synthesis of fluorescent lactosylceramide stereoisomers
  作者：Yidong Liu、Robert Bittman

  DOI：10.1016/j.chemphyslip.2006.03.001

  日期：2006.7

  The intracellular distribution of synthetic glycosphingolipids (GSLs) bearing a fluorophore can be monitored in living cells by fluorescence microscopy. We reported previously that variation in the length of the long-chain base and in the structure of the carbohydrate-containing polar head group of (2S,3R) (or D-erythro-)-beta-lactosylceramide (LacCer) did not alter the mechanism of endocytic uptake from the plasma membrane of various mammalian cell types [Singh, R.D., Puri, V., Valiyaveettil, J.T., Marks, D.L., Bittman, R., Pagano, R.E., 2003. Selective caveolin-l-dependent endocytosis of glycosphingolipids. Mol. Biol. Cell 14, 3254-3265]. To extend our examination of the molecular features in LacCer that are responsible for its uptake by the caveolar-requiring endocytic pathway, we have synthesized the three unnatural stereoisomers [(2R,3R)-, (2S,3S)-, and (2R,3S)] of dipyrromethene difluoride (BODIPY (TM))-LacCer. These analogues will be used to probe the role of stereochemistry in the long-chain base of LacCer in the mechanism of endocytic uptake. (c) 2006 Elsevier Ireland Ltd. All rights reserved.