N-己酰基-D-鞘磷脂 | 182493-45-4

• 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-己酰基-D-鞘磷脂
• 英文名称: N-hexanoylsphingosine-1-phosphocholine
• 英文别名: [(E,2S,3R)-2-(hexanoylamino)-3-hydroxyoctadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 182493-45-4
• 化学式: C29H59N2O6P
• 分子量: 562.8
• InChiKey: AHZZHULAOVWYNO-RRKDMDGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  38
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-己酰基-D-鞘磷脂 生成 胆碱 、 N-hexanoyl-sphingosine-1,3-cyclophosphate(1-)
  参考文献：
  名称：

  Phospholipase D Toxins of Brown Spider Venom Convert Lysophosphatidylcholine and Sphingomyelin to Cyclic Phosphates

  摘要：

  Loxosceles属棕蜘蛛的毒液中含有磷脂酶D酶毒素，可导致严重皮肤坏死，甚至导致人类死亡。这些毒素会分解哺乳动物组织中的鞘氨醇和溶血磷脂酰胆碱，释放胆碱头基。此前有报道称，分解底物的其他产物是单酯磷脂，这是底物水解的结果。我们使用31P NMR和质谱技术证明，重组毒素以及来自不同Loxosceles物种的完整毒液仅催化转磷酸化，而不是水解，从两种主要底物形成环状磷酸盐产物。环状磷酸盐与单酯磷酸盐具有截然不同的生物特性，可能与棕蜘蛛毒液致病有关。

  DOI：

  10.1371/journal.pone.0072372

文献信息

• Variable Substrate Preference among Phospholipase D Toxins from Sicariid Spiders
  作者：Daniel M. Lajoie、Sue A. Roberts、Pamela A. Zobel-Thropp、Jared L. Delahaye、Vahe Bandarian、Greta J. Binford、Matthew H.J. Cordes

  DOI：10.1074/jbc.m115.636951

  日期：2015.4

  Venoms of the sicariid spiders contain phospholipase D enzyme toxins that can cause severe dermonecrosis and even death in humans. These enzymes convert sphingolipid and lysolipid substrates to cyclic phosphates by activating a hydroxyl nucleophile present in both classes of lipid. The most medically relevant substrates are thought to be sphingomyelin and/or lysophosphatidylcholine. To better understand the substrate preference of these toxins, we used P-31 NMR to compare the activity of three related but phylogenetically diverse sicariid toxins against a diverse panel of sphingolipid and lysolipid substrates. Two of the three showed significantly faster turnover of sphingolipids over lysolipids, and all three showed a strong preference for positively charged (choline and/or ethanolamine) over neutral (glycerol and serine) headgroups. Strikingly, however, the enzymes vary widely in their preference for choline, the headgroup of both sphingomyelin and lysophosphatidylcholine, versus ethanolamine. An enzyme from Sicarius terrosus showed a strong preference for ethanolamine overcholine, whereas two paralogous enzymes from Loxosceles arizonica either preferred choline or showed no significant preference. Intrigued by the novel substrate preference of the Sicarius enzyme, we solved its crystal structure at 2.1 angstrom resolution. The evolution of variable substrate specificity may help explain the reduced dermonecrotic potential of some natural toxin variants, because mammalian sphingolipids use primarily choline as a positively charged headgroup; it may also be relevant for sicariid predatory behavior, because ethanolamine-containing sphingolipids are common in insect prey.