N-二十四酰植物鞘胺醇 | 34437-74-6

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 中文名称: N-二十四酰植物鞘胺醇
• 英文名称: (2S,3S,4R)-2-tetracosanoylamino-1,3,4-octadecanetriol
• 英文别名: N-tetracosanoylphytosphingosine；N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]tetracosanamide
• CAS: 34437-74-6
• 化学式: C₄₂H₈₅NO₄
• 分子量: 668.141
• InChiKey: ZESJDNWGTANZCC-LFVSMIGWSA-N

物化性质

• 溶解度：
  氯仿:甲醇(5:1):可溶

计算性质

• 辛醇/水分配系数(LogP)：
  16.6
• 重原子数：
  47
• 可旋转键数：
  39
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  N-二十四酰植物鞘胺醇 、 三苯基氯甲烷 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 3.0h， 生成 (2S,3S,4R)-N-tetracosanoyl-1-O-triphenylmethyl-2-amino-1,3,4-octadecanetriol
  参考文献：
  名称：

  Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice

  摘要：

  Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2-[N-((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S;4R)-1-O-(alpha-D-galactopyranosyl)2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.

  DOI：

  10.1021/jm00012a018
• 作为产物：
  描述：

  (2S,3S,4R)-2-amino-1,3,4-tribenzyloxyoctadecane 在 palladium on activated charcoal 三正丁胺 、 2-氯-1-甲基吡啶碘化物 、 氢气 作用下， 以 四氢呋喃 、 丙醇 、 甲酸 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-二十四酰植物鞘胺醇
  参考文献：
  名称：

  Koike, Katsuya; Nakahara, Yoshiaki; Ogawa, Tomoya, Agricultural and Biological Chemistry, 1990, vol. 54, # 3, p. 663 - 667

  摘要：

  DOI：

文献信息

• Substrate specificity, kinetic properties and inhibition by fumonisin B1 of ceramide synthase isoforms from Arabidopsis
  作者：Kyle D. Luttgeharm、Edgar B. Cahoon、Jonathan E. Markham

  DOI：10.1042/bj20150824

  日期：2016.3.1

  Ceramides are organizing components of sphingolipids in the eukaryotic cell. Three ceramide synthase isoforms are found in Arabidopsis thaliana each with specific substrate preferences and sensitivity to inhibitors and activators.

  神经酰胺是真核细胞中鞘磷脂的组织成分。拟南芥中有三种神经酰胺合成酶异构体，每种异构体都有特定的底物偏好以及对抑制剂和激活剂的敏感性。
• Koike, Katsuya; Nakahara, Yoshiaki; Ogawa, Tomoya, Agricultural and Biological Chemistry, 1990, vol. 54, # 3, p. 663 - 667
  作者：Koike, Katsuya、Nakahara, Yoshiaki、Ogawa, Tomoya

  DOI：——

  日期：——
• KOIKE, KATSUYA;NAKAHARA, YOSHIAKI;OGAWA, TOMOYA, AGR. AND BIOL. CHEM., 54,(1990) N, C. 663-667
  作者：KOIKE, KATSUYA、NAKAHARA, YOSHIAKI、OGAWA, TOMOYA

  DOI：——

  日期：——
• C26-CoA-dependent ceramide synthesis of Saccharomyces cerevisiae is operated by Lag1p and Lac1p
  作者：I. Guillas

  DOI：10.1093/emboj/20.11.2655

  日期：2001.6.1

  Lag1p and Lac1p are two highly homologous membrane proteins of the endoplasmic reticulum (ER). When both genes are deleted, cells cannot transport glycosylphosphatidylinositol (GPI)-anchored proteins from the ER to the Golgi at a normal rate. Here we show that microsomes or detergent extracts from lag1 Delta lac1 Delta double mutants lack an activity transferring C26 fatty acids from C26-coenzyme A onto dihgdrosphingosine or phytosphingosine. As a consequence, in intact cells, the normal ceramides and inositolphosphorylceramides are drastically reduced. lag1 Delta lacl Delta cells compensate for the lack of normal sphingolipids by making increased amounts of C26 fatty acids, which become incorporated into glycerophospholipids. They also contain 20- to 25-fold more free long chain bases than wild type and accumulate very large amounts of abnormally polar ceramides, They make small amounts of abnormal mild base-resistant inositolphospholipids. The lipid remodelling of GPI-anchored proteins is severely compromised in lag1 Delta lac1 Delta double mutants since only few and mostly abnormal ceramides are incorporated into the GPI anchors. The participation of Lag1p and Lac1p in ceramide synthesis may explain their role in determining longevity.
• Cloning of an Alkaline Ceramidase from Saccharomyces cerevisiae
  作者：Cungui Mao、Ruijuan Xu、Alicja Bielawska、Lina M. Obeid

  DOI：10.1074/jbc.275.10.6876

  日期：2000.3

  Ceramide is not only a core intermediate of sphingolipids but also an important modulator of many cellular events including apoptosis, cell cycle arrest, senescence, differentiation, and stress responses. Its turnover may be tightly regulated. However, little is known about the regulation of its metabolism because most enzymes responsible for its synthesis and breakdown have yet to be cloned. Here we report the cloning and characterization of the yeast gene YPC1 (YBR183w) by screening Saccharomyces cerevisiae genes whose overexpression bestows resistance to fumonisin B1. We demonstrate that the yeast gene YPC1 encodes an alkaline ceramidase activity responsible for the breakdown of dihydroceramide and phytoceramide but not unsaturated ceramide. YPC1 ceramidase activity was confirmed by in vitro studies using an Escherichia coli expression system. Importantly, YPC1p also has reverse activity, catalyzing synthesis of phytoceramide from palmitic acid and phytosphingosine. This ceramide synthase activity is CoA-independent and is resistant to fumonisin B1, thus explaining why YPC1 was cloned as a fumonisin B1-resistant gene.