cer(d18:0/12:0)

• 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: cer(d18:0/12:0)
• 英文别名: N-dodecanoylsphinganine；N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]dodecanamide
• 化学式: C₃₀H₆₁NO₃
• 分子量: 483.819
• InChiKey: UHWYQXNZIBLESO-URLMMPGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  34
• 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：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  水 、 cer(d18:0/12:0) 生成 laurate anion 、 Sphinganine(1+)
  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：

  月桂酰氯 、 D-赤式-二氢-D-鞘氨醇 在 吡啶 作用下， 以 N-甲基吡咯烷酮 、 四氢呋喃 为溶剂， 生成 cer(d18:0/12:0)
  参考文献：
  名称：

  The Synthesis and Biological Characterization of a Ceramide Library

  摘要：

  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.

  DOI：

  10.1021/ja017576o

文献信息

• PROCESS FOR PREPARING SPHINGOLIPIDS
  申请人：Evonik Degussa GmbH

  公开号：US20190300917A1

  公开（公告）日：2019-10-03

  The invention provides a process for preparing sphingolipids, compositions comprising sphingolipids and further components, and for the use of the compositions.

  这项发明提供了一种制备鞘脂类物质的过程，包括鞘脂类物质和其他成分的组合物，并用于这些组合物的用途。
• [EN] ARTIFICIALLY SYNTHESIZED SPHINGOSINE DERIVATIVE LIPOID MONOMER AND USE OF SAME FOR DELIVERING NUCLEIC ACID<br/>[FR] MONOMÈRE LIPOÏDE DÉRIVÉ DE SPHINGOSINE SYNTHÉTISÉ ARTIFICIELLEMENT ET SON UTILISATION POUR L'ADMINISTRATION D'ACIDE NUCLÉIQUE<br/>[ZH] 人工合成的鞘氨醇衍生物类脂质单体及其递送核酸的用途
  申请人：INST BASIC MEDICAL SCIENCES CAMS

  公开号：WO2019185038A1

  公开（公告）日：2019-10-03

  本发明提供了人工合成的鞘氨醇类脂质单体及其递送核酸的用途。具体地，本发明提供了使用式I化合物、其立体异构体或其药学上可接受的盐或包含式I的化合物、其立体异构体或其药学上可接受的盐的组合对细胞或受试者递送核酸的用途或方法，(I)
• II. Synthesis of Long Chain Fatty Acid Amines of Sphingosine and Dihydrosphingosine¹
  作者：Benjamin Weiss、Paula Raizman

  DOI：10.1021/ja01550a061

  日期：1958.9
• Keratin fiber strengthening agent and method for strengthening keratin fiber
  申请人：Takasago International Corporation

  公开号：EP0920852B1

  公开（公告）日：2005-06-01
• US6379659B1
  申请人：——

  公开号：US6379659B1

  公开（公告）日：2002-04-30