N-dodecanoyl phytosphingosine

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: N-dodecanoyl phytosphingosine
• 英文别名: N-dodecanoylphytosphingosine；N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]dodecanamide
• 化学式: C₃₀H₆₁NO₄
• 分子量: 499.819
• InChiKey: NGPJDSJKORHGMX-LXQNXJGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  35
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  水 、 N-dodecanoyl phytosphingosine 生成 Phytosphingosine(1+) 、 laurate anion
  参考文献：
  名称：

  The Reverse Activity of Human Acid Ceramidase

  摘要：

  An overexpression system was recently developed to produce and purify recombinant, human acid ceramidase. In addition to ceramide hydrolysis, the purified enzyme was able to catalyze ceramide synthesis using [C-14] lauric acid and sphingosine as substrates. Herein we report detailed characterization of this acid ceramidase-associated "reverse activity" and provide evidence that this reaction occurs in situ as well as in vitro. The pH optimum of the reverse reaction was similar to5.5, as compared with similar to4.5 for the hydrolysis reaction. Non-ionic detergents and zinc cations inhibited the activity, whereas most other cations were stimulatory. Of note, sphingomyelin also was very inhibitory toward this reaction, whereas the anionic lipids, phosphatidic acid and phosphatidylserine, were stimulatory. Of various sphingosine stereoisomers tested in the reverse reaction, only the natural, D-erythro form could efficiently serve as a substrate. Using D-erythro-sphingosine and lauric acid as substrates, the reaction followed normal Michaelis-Menten kinetics. The K-m and V-max values toward sphingosine were 23.75 muM and 208.3 pmol/mug/h, respectively, whereas for lauric acid they were 73.76 muM and 232.5 pmol/mug/h, respectively. Importantly, the reverse activity was reduced in cell lysates from a Farber disease patient to the same extent as the acid ceramidase activity. Furthermore, when 12-(N-methyl-N-(7-nitrobenz-2- oxa-1,3-diazol-4-yl)) (NBD)-conjugated lauric acid and sphingosine were added to cultured lymphoblasts from a Farber disease patient in the presence of fumonisin B ( 1), the conversion to NBD-ceramide was reduced similar to30% when compared with normal cells. These data provide important new information on human acid ceramidase and further document its central role in sphingolipid metabolism.

  DOI：

  10.1074/jbc.m303310200
• 作为产物：
  描述：

  糖脂 、 月桂酸甲酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以83.5%的产率得到N-dodecanoyl phytosphingosine
  参考文献：
  名称：

  METHOD FOR PRODUCING N-ACYLAMINO TRIOL DERIVATIVES

  摘要：

  公开号：

  EP2757090B1

文献信息

• The Synthesis and Biological Characterization of a Ceramide Library
  作者：Young-Tae Chang、Jaehwa Choi、Sheng Ding、Eva E. Prieschl、Thomas Baumruker、Jae-Mok Lee、Sung-Kee Chung、Peter G. Schultz

  DOI：10.1021/ja017576o

  日期：2002.3.1

  A facile synthesis of a combinatorial ceramide library and their activities in the NF-kappaB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-kappaB activating molecule was discovered among ceramide containing beta-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated.
• METHOD FOR PRODUCING N-ACYLAMINO TRIOL DERIVATIVES
  申请人：Kao Corporation

  公开号：EP2757090B1

  公开（公告）日：2017-04-26
• The Reverse Activity of Human Acid Ceramidase
  作者：Nozomu Okino、Xingxuan He、Shimon Gatt、Konrad Sandhoff、Makoto Ito、Edward H. Schuchman

  DOI：10.1074/jbc.m303310200

  日期：2003.8

  An overexpression system was recently developed to produce and purify recombinant, human acid ceramidase. In addition to ceramide hydrolysis, the purified enzyme was able to catalyze ceramide synthesis using [C-14] lauric acid and sphingosine as substrates. Herein we report detailed characterization of this acid ceramidase-associated "reverse activity" and provide evidence that this reaction occurs in situ as well as in vitro. The pH optimum of the reverse reaction was similar to5.5, as compared with similar to4.5 for the hydrolysis reaction. Non-ionic detergents and zinc cations inhibited the activity, whereas most other cations were stimulatory. Of note, sphingomyelin also was very inhibitory toward this reaction, whereas the anionic lipids, phosphatidic acid and phosphatidylserine, were stimulatory. Of various sphingosine stereoisomers tested in the reverse reaction, only the natural, D-erythro form could efficiently serve as a substrate. Using D-erythro-sphingosine and lauric acid as substrates, the reaction followed normal Michaelis-Menten kinetics. The K-m and V-max values toward sphingosine were 23.75 muM and 208.3 pmol/mug/h, respectively, whereas for lauric acid they were 73.76 muM and 232.5 pmol/mug/h, respectively. Importantly, the reverse activity was reduced in cell lysates from a Farber disease patient to the same extent as the acid ceramidase activity. Furthermore, when 12-(N-methyl-N-(7-nitrobenz-2- oxa-1,3-diazol-4-yl)) (NBD)-conjugated lauric acid and sphingosine were added to cultured lymphoblasts from a Farber disease patient in the presence of fumonisin B ( 1), the conversion to NBD-ceramide was reduced similar to30% when compared with normal cells. These data provide important new information on human acid ceramidase and further document its central role in sphingolipid metabolism.