(2S,3R)-2-aminopent-4-ene-1,3-diol | 631090-33-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3R)-2-aminopent-4-ene-1,3-diol
• CAS: 631090-33-0
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: YYAPFWJOYCVYIV-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-aminopent-4-ene-1,3-diol 在 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Development of a new doubly-labeled fluorescent ceramide probe for monitoring the metabolism of sphingolipids in living cells

  摘要：

  A new ceramide analog, 1, containing two fluorescent dyes, NBD in the N-acyl part and KFL5 in the alkyl part, was synthesized. The fluorescence from both NBD and KFL5 was detected in living cells in a time-dependent manner. A multi-wavelength fluorescence detector was used to detect ceramide metabolites including sphingosine, sphingosine-l-phosphate, glucosylceramide, and sphingomyelin, which are connected to the fluorescent dyes, simultaneously in a single TLC plate.

  DOI：

  10.1016/j.bmcl.2018.08.013
• 作为产物：
  描述：

  tert-butyl ((2S,3R)-1,3-dihydroxypent-4-en-2-yl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (2S,3R)-2-aminopent-4-ene-1,3-diol
  参考文献：
  名称：

  脂质体 FRET 测定鉴定神经酰胺转运蛋白 (CERT) 的有效药物样抑制剂

  摘要：

  神经酰胺转移蛋白（CERT）介导神经酰胺从内质网到高尔基体的非囊泡转移，从而催化鞘磷脂生物合成的限速步骤。通常，CERT 配体在繁琐的结合测定或使用放射性标记神经酰胺的非均相转移测定中进行评估。本文提出了一种基于福斯特共振能量转移 (FRET) 的简单且灵敏的 CERT 检测方法。为此，我们混合了供体和受体囊泡，每个囊泡含有不同的荧光神经酰胺种类。通过 CERT 介导的荧光神经酰胺转移，建立了 FRET 系统，尽管组件具有高疏水性，但仍可以在 96 孔板格式中进行读数。对 2000 种化合物库的筛选产生了两种新的有效 CERT 抑制剂。一种被批准用于人类，另一种被批准用于动物。通过定量质谱和共聚焦显微镜对细胞活性的评估表明，神经酰胺运输和鞘磷脂生物合成受到抑制。

  DOI：

  10.1002/chem.202003283

文献信息

• [EN] SYNTHETIC METHODS FOR THE LARGE SCALE PRODUCTION FROM GLUCOSE OF ANALOGS OF SPHINGOSINE, AZIDOSPHINGOSINE, CERAMIDES, LACTOSYL CERAMIDES, AND GLYCOSYL PHYTOSPHINGOSINE<br/>[FR] METHODES DE SYNTHESE PERMETTANT LA PRODUCTION A GRANDE ECHELLE A PARTIR DE GLUCOSE D'ANALOGUES DE SPHINGOSINE, AZIDOSPHINGOSINE, CERAMIDES, LACTOSYLCERAMIDES, ET GLYCOSYLE PHYTOSPHINGOSINE
  申请人：BUNDLE DAVID R

  公开号：WO2003101937A1

  公开（公告）日：2003-12-11

  Synthetic methods are disclosed for the production from glucose of analogs of sphingosine, azidosphingosine, ceramides, lactosyl ceramides, glycosyl phytosphingosine, and enantiomeric derivatives of phytosphingosine and/or its homologues, for use in pharmaceutical applications. The disclosed syntheses are simple, direct and easily scaled.

  揭示了一种从葡萄糖生产类似物的合成方法，包括鞘氨醇、偶氮鞘氨醇、酰胺、乳糖基酰胺、糖基植物鞘氨醇以及植物鞘氨醇及/或其同系物的对映体衍生物，用于药物应用。所揭示的合成方法简单、直接且易于扩展。
• A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs
  作者：Ye Cai、Chang-Chun Ling、David R. Bundle

  DOI：10.1039/b516333a

  日期：——

  Sphingosine, sphinganines and phytosphingosines and their analogs were synthesized by an aldol condensation between an iminoglycinate bearing a (+)-(1R,2R,5R)-2-hydroxy-3-pinanone group as chiral auxiliary and an appropriate aldehyde. All condensations proceeded with excellent enantioselectivity to generate the (2S,3R)-D-erythro structures in good yields.

  鞘氨醇，鞘氨醇和植物鞘氨醇及其类似物是通过带有（+）-（1R，2R，5R）-2-羟基-3-吡喃酮基作为手性助剂的亚氨基甘氨酸酸酯与适当的醛之间的醛醇缩合合成的。所有缩合以优异的对映选择性进行，以高收率产生（2S，3R）-D-赤型结构。
• Sphingosine and clavaminol H derivatives bearing fluorinated chains and their cytotoxic activity
  作者：Eva Prchalová、Ivan Votruba、Martin Kotora

  DOI：10.1016/j.jfluchem.2012.06.005

  日期：2012.9

  Microwave induced cross-metathesis of perfluoroalkylated propenes with a substituted allyl alcohol is a simple and straightforward method for the synthesis of sphingosine derivatives possessing perfluoroalkyl chains. One of the prepared compounds was converted into the fluorinated clavaminol H derivative and its deacetylated congener. Selected compounds were subjected to preliminary testing for cytotoxic activity on several cancer cell lines. (C) 2012 Elsevier B.V. All rights reserved.
• Development of a new doubly-labeled fluorescent ceramide probe for monitoring the metabolism of sphingolipids in living cells
  作者：Yabin Wang、Junya Kasahara、Kazuyuki Yamagata、Hiroyuki Nakamura、Toshihiko Murayama、Noriyuki Suzuki、Atsushi Nishida

  DOI：10.1016/j.bmcl.2018.08.013

  日期：2018.10

  A new ceramide analog, 1, containing two fluorescent dyes, NBD in the N-acyl part and KFL5 in the alkyl part, was synthesized. The fluorescence from both NBD and KFL5 was detected in living cells in a time-dependent manner. A multi-wavelength fluorescence detector was used to detect ceramide metabolites including sphingosine, sphingosine-l-phosphate, glucosylceramide, and sphingomyelin, which are connected to the fluorescent dyes, simultaneously in a single TLC plate.
• Liposomal FRET Assay Identifies Potent Drug‐Like Inhibitors of the Ceramide Transport Protein (CERT)
  作者：Doaa Samaha、Housam H. Hamdo、Xiaojing Cong、Fabian Schumacher、Sebastian Banhart、Öznur Aglar、Heiko M. Möller、Dagmar Heuer、Burkhard Kleuser、Essa M. Saied、Christoph Arenz

  DOI：10.1002/chem.202003283

  日期：2020.12.15

  Ceramide transfer protein (CERT) mediates non‐vesicular transfer of ceramide from endoplasmic reticulum to Golgi apparatus and thus catalyzes the rate‐limiting step of sphingomyelin biosynthesis. Usually, CERT ligands are evaluated in tedious binding assays or non‐homogenous transfer assays using radiolabeled ceramides. Herein, a facile and sensitive assay for CERT, based on Förster resonance energy

  神经酰胺转移蛋白（CERT）介导神经酰胺从内质网到高尔基体的非囊泡转移，从而催化鞘磷脂生物合成的限速步骤。通常，CERT 配体在繁琐的结合测定或使用放射性标记神经酰胺的非均相转移测定中进行评估。本文提出了一种基于福斯特共振能量转移 (FRET) 的简单且灵敏的 CERT 检测方法。为此，我们混合了供体和受体囊泡，每个囊泡含有不同的荧光神经酰胺种类。通过 CERT 介导的荧光神经酰胺转移，建立了 FRET 系统，尽管组件具有高疏水性，但仍可以在 96 孔板格式中进行读数。对 2000 种化合物库的筛选产生了两种新的有效 CERT 抑制剂。一种被批准用于人类，另一种被批准用于动物。通过定量质谱和共聚焦显微镜对细胞活性的评估表明，神经酰胺运输和鞘磷脂生物合成受到抑制。