C24:0 galactosyl(β)ceramide | 74645-26-4

• 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: C24:0 galactosyl(β)ceramide
• 英文别名: beta-D-galactosyl-N-(tetracosanoyl)sphingosine；N-[(E,2S,3R)-3-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]tetracosanamide
• CAS: 74645-26-4
• 化学式: C₄₈H₉₃NO₈
• 分子量: 812.268
• InChiKey: POQRWMRXUOPCLD-HIIAJUEOSA-N

物化性质

• 沸点：
  902.1±65.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.6
• 重原子数：
  57
• 可旋转键数：
  41
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  C24:0 galactosyl(β)ceramide 在 臭氧 作用下， 以 氯仿 为溶剂， 生成 肉豆蔻醛
  参考文献：
  名称：

  对角蛋白和神经胶的结构知识的贡献

  摘要：

  分离出的Kerasin Myristaldehyd，肉豆蔻酸和D-赤藓醇中的臭氧消耗量为-3-氨基-2-羟基-γ-丁内酯盐酸盐。

  DOI：

  10.1002/hlca.19600430745
• 作为产物：
  描述：

  木焦油酸 在 TEA 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 C24:0 galactosyl(β)ceramide
  参考文献：
  名称：

  Quantitative Measurements of Recombinant HIV Surface Glycoprotein 120 Binding to Several Glycosphingolipids Expressed in Planar Supported Lipid Bilayers

  摘要：

  The interaction of recombinant HIV-1 surface glycoprotein gp120 (rgp120) with natural isolates of lactosylceramide (LacCer), glucosylceramide (GlcCer), and galactosylceramide (GaiCer) has been quantitatively measured under equilibrium conditions using total internal reflection fluorescence (TIRF) spectroscopy. The binding affinity (K-a) of rgp120 to these glycosphingolipids (GSLs), reconstituted at 5 mol % in supported planar lipid bilayers composed of 95 mol % POPC, is ca. 10(6) M-1 for dissolved rgp120 concentrations greater than 25 nM. In contrast, at concentrations of rgp120 between 0.2 and 15 nM, rgp120 does not bind significantly to LacCer and GlcCer, but has a high affinity for GalCer with a measured K-a value of 1.6 x 10(9) M-1. However, protein surface coverage measurements show that this strong binding process accounts for very little of the total protein adsorbed over the entire concentration range studied. At a protein concentration of ca. 20 nM, the surface coverage is only 3% of that achieved at apparent saturation (i.e., when the protein concentration is ca. 220 nM). Thus the "high affinity" binding sites comprise only a small fraction of the total number of binding sites. Several other variables were investigated, Rgp120 binding behavior at membranes doped with alpha-hydroxygalactosylceramide (alpha-GalCer) was very similar to that observed with GalCer, showing that the presence/absence of an alpha-hydroxy moiety does not significantly affect galactosylceramide recognition. Phase segregation of GalCer, which occurs when the mole fraction of this GSL in a POPC bilayer exceeds ca. 0.1, was also investigated and showed no effect on binding affinity at low rgp120 concentrations. To investigate the influence of fatty acid chain length, GSLs with monodisperse C-18 and C-24 chain lengths, both with and without an alpha-hydroxy moiety, were synthesized, and their binding affinity to rgp120 was examined. Relative to the natural isolates (which contain a mixture of chain lengths), minimal differences were observed; thus among the compounds tested, fatty acid chain length does not affect GSL recognition. The results of this work should aid efforts to design anti-HIV-1 agents based on membrane-tethered, carbohydrate-based receptors for rgp120.

  DOI：

  10.1021/ja011225s

文献信息

• Klenk; Haerle, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1930, vol. 189, p. 243,248, 249
  作者：Klenk、Haerle

  DOI：——

  日期：——
• Chargaff, Journal of Biological Chemistry, 1937, vol. 121, p. 187,190, 191
  作者：Chargaff

  DOI：——

  日期：——
• Beiträge zur Kenntnis der Struktur des Kerasins und des Nervons
  作者：J. Kiss、D. Bánfi、J. Kóbor

  DOI：10.1002/hlca.19600430745

  日期：——

  Es wurden beim Ozonabbau von Kerasin Myristaldehyd, Myristinsäure und D-erythro-3-Amino-2-hydroxy-γ-butyrolacton-hydrochlorid isoliert.

  分离出的Kerasin Myristaldehyd，肉豆蔻酸和D-赤藓醇中的臭氧消耗量为-3-氨基-2-羟基-γ-丁内酯盐酸盐。
• Quantitative Measurements of Recombinant HIV Surface Glycoprotein 120 Binding to Several Glycosphingolipids Expressed in Planar Supported Lipid Bilayers
  作者：John C. Conboy、Katherine D. McReynolds、Jacquelyn Gervay-Hague、S. Scott Saavedra

  DOI：10.1021/ja011225s

  日期：2002.2.1

  The interaction of recombinant HIV-1 surface glycoprotein gp120 (rgp120) with natural isolates of lactosylceramide (LacCer), glucosylceramide (GlcCer), and galactosylceramide (GaiCer) has been quantitatively measured under equilibrium conditions using total internal reflection fluorescence (TIRF) spectroscopy. The binding affinity (K-a) of rgp120 to these glycosphingolipids (GSLs), reconstituted at 5 mol % in supported planar lipid bilayers composed of 95 mol % POPC, is ca. 10(6) M-1 for dissolved rgp120 concentrations greater than 25 nM. In contrast, at concentrations of rgp120 between 0.2 and 15 nM, rgp120 does not bind significantly to LacCer and GlcCer, but has a high affinity for GalCer with a measured K-a value of 1.6 x 10(9) M-1. However, protein surface coverage measurements show that this strong binding process accounts for very little of the total protein adsorbed over the entire concentration range studied. At a protein concentration of ca. 20 nM, the surface coverage is only 3% of that achieved at apparent saturation (i.e., when the protein concentration is ca. 220 nM). Thus the "high affinity" binding sites comprise only a small fraction of the total number of binding sites. Several other variables were investigated, Rgp120 binding behavior at membranes doped with alpha-hydroxygalactosylceramide (alpha-GalCer) was very similar to that observed with GalCer, showing that the presence/absence of an alpha-hydroxy moiety does not significantly affect galactosylceramide recognition. Phase segregation of GalCer, which occurs when the mole fraction of this GSL in a POPC bilayer exceeds ca. 0.1, was also investigated and showed no effect on binding affinity at low rgp120 concentrations. To investigate the influence of fatty acid chain length, GSLs with monodisperse C-18 and C-24 chain lengths, both with and without an alpha-hydroxy moiety, were synthesized, and their binding affinity to rgp120 was examined. Relative to the natural isolates (which contain a mixture of chain lengths), minimal differences were observed; thus among the compounds tested, fatty acid chain length does not affect GSL recognition. The results of this work should aid efforts to design anti-HIV-1 agents based on membrane-tethered, carbohydrate-based receptors for rgp120.