D-核C20-植物鞘氨醇 | 3530-53-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: D-核C20-植物鞘氨醇
• 英文名称: (2S,3S,4R)-2-amino-1,3,4-eicosaneanetriol
• 英文别名: (2S,3S,4R)-2-aminoeicosane-1,3,4-triol；(2S,3S,4R)-2-aminoicosane-1,3,4-triol；D-ribo-C(20)-phytosphingosine
• CAS: 3530-53-8
• 化学式: C₂₀H₄₃NO₃
• 分子量: 345.566
• InChiKey: UQAUXYMLKGFKBX-ZCNNSNEGSA-N

物化性质

• 熔点：
  101-103 °C
• 沸点：
  507.3±45.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  二十二酰氯 、 D-核C20-植物鞘氨醇 在 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以95%的产率得到(2S,3S,4R)-2-docosanoylamino-1,3,4-eicosanetriol
  参考文献：
  名称：

  Wild, Robert; Schmidt, Richard R., Liebigs Annalen, 1995, # 5, p. 755 - 764

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,3S,4R)-2-azido-1,3,4-tri-O-benzyl-1,3,4-eicosanetriol 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 以80%的产率得到D-核C20-植物鞘氨醇
  参考文献：
  名称：

  Wild, Robert; Schmidt, Richard R., Liebigs Annalen, 1995, # 5, p. 755 - 764

  摘要：

  DOI：

文献信息

• A facile synthesis of d-ribo-C20-phytosphingosine and its C2 epimer from d-ribose
  作者：Miroslava Martinková、Jozef Gonda、Kvetoslava Pomikalová、Jozef Kožíšek、Juraj Kuchár

  DOI：10.1016/j.carres.2011.05.028

  日期：2011.9

  A facile synthetic route to d-ribo-C(20)-phytosphingosine 31 and its C2 epimer 32 is described. The Overman rearrangement of allylic trichloroacetimidates derived from the known ribose derivative 7 has been used as the key step. The subsequent functional group interconversions in rearranged products 14 and 15 followed by Wittig olefination, Pd/C-mediated reduction and the removal of protecting groups

  描述了一种容易的合成途径，用于合成d-核糖-C（20）-植物鞘氨醇31及其C2差向异构体32。衍生自已知核糖衍生物7的烯丙基三氯乙亚氨酸酯的超载重排已用作关键步骤。重排产物14和15中随后的官能团相互转化，然后进行维蒂希烯化，Pd / C介导的还原和保护基的去除，成功地构建了最终分子。
• Method for producing acetylated sphingoid base
  申请人：Kao Corporation

  公开号：US10066249B2

  公开（公告）日：2018-09-04

  Provided is a means for producing an acetylated sphingoid base using modified microorganism in the genus Starmerella, particularly Starmerella bombicola. A method for producing an acetylated sphingoid base comprising culturing a microorganism in the genus Starmerella to which a xenogeneic gene encoding a polypeptide having an activity to acetylate a sphingoid base is introduced.

  本发明提供了一种利用改良星菌属微生物，特别是星菌 bombicola 生产乙酰化鞘氨醇碱的方法。生产乙酰化类鞘磷脂碱的方法包括培养星菌属微生物，在该微生物中引入编码具有乙酰化类鞘磷脂碱活性的多肽的异源基因。
• Mutant endoglycoceramidases with enhanced synthetic activity
  申请人：La Jolla Pharmaceutical Company

  公开号：US10294504B2

  公开（公告）日：2019-05-21

  The present invention relates to a novel endoglycoceramidase whose hydrolytic activity has been substantially reduced or eliminated, such that the enzyme is useful for synthesis of glycolipids from a monosaccharide or oligosaccharide and a ceramide. More specifically, the endoglycoceramidase is a mutant version of a naturally occurring endoglycoceramidase, preferably comprising a mutation within the active site or the nucleophilic site of the enzyme and more preferably comprising a substitution mutation of the Glu residue within the active site or the nucleophilic site. Also disclosed are a method for generating the mutant endoglycoceramidase and a method for enzymatically synthesizing glycolipids using this mutant enzyme.

  本发明涉及一种新型内聚甘糖苷酶，其水解活性已大大降低或消除，因此该酶可用于由单糖或寡糖和神经酰胺合成糖脂。更具体地说，内糖化酶是天然存在的内糖化酶的突变体，优选包括酶的活性位点或亲核位点内的突变，更优选包括活性位点或亲核位点内 Glu 残基的取代突变。还公开了一种产生突变型内糖化酶的方法和一种使用这种突变型酶酶解合成糖脂的方法。
• METHOD FOR PRODUCING ACETYLATED SPHINGOID BASE
  申请人：Kao Corporation

  公开号：EP3071700B1

  公开（公告）日：2022-07-20
• Mutant Endoglycoceramidases With Enhanced Synthetic Activity
  申请人：Johnson Karl F.

  公开号：US20090170155A1

  公开（公告）日：2009-07-02

  The present invention relates to a novel endoglycoceramidase whose hydrolytic activity has been substantially reduced or eliminated, such that the enzyme is useful for synthesis of glycolipids from a monosaccharide or oligosaccharide and a ceramide. More specifically, the endoglycoceramidase is a mutant version of a naturally occurring endoglycoceramidase, preferably comprising a mutation within the active site or the nucleophilic site of the enzyme and more preferably comprising a substitution mutation of the Glu residue within the active site or the nucleophilic site. Also disclosed are a method for generating the mutant endoglycoceramidase and a method for enzymatically synthesizing glycolipids using this mutant enzyme.