(2S,3R,4E)-1-O-<(α-D-galactopyranosyl)-(1->4)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosyloxy>-2-(hexadecanoylamino)-4-octadecen-3-ol | 137896-85-6

• 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: (2S,3R,4E)-1-O-<(α-D-galactopyranosyl)-(1->4)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosyloxy>-2-(hexadecanoylamino)-4-octadecen-3-ol
• 英文别名: globotriaosylceramide；1-O-(α-Gal-4-β-Gal-4-β-Glc)ceramide d18:1/C16:0；alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/16:0)；N-[(E,2S,3R)-1-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxyoctadec-4-en-2-yl]hexadecanamide
• CAS: 137896-85-6
• 化学式: C₅₂H₉₇NO₁₈
• 分子量: 1024.34
• InChiKey: MGOOTGNGBOPVIV-VVNLPLDBSA-N

物化性质

• 沸点：
  1122.3±65.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿:甲醇(2:1)：可溶； DMSO：可溶；甲醇：温热的

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  71
• 可旋转键数：
  39
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  307
• 氢给体数：
  12
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  (2S,3R,4E) 2-azido-3-(benzoyloxy)-2-(hexadecanoylamino)-1-O-<(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>-4-octadecene 在 四氢呋喃 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以98%的产率得到(2S,3R,4E)-1-O-<(α-D-galactopyranosyl)-(1->4)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosyloxy>-2-(hexadecanoylamino)-4-octadecen-3-ol
  参考文献：
  名称：

  Qiu, Dongxu; Schmidt, Richard R., Liebigs Annalen der Chemie, 1992, # 3, p. 217 - 224

  摘要：

  DOI：

文献信息

• Synthesis of a Panel of Carbon-13-Labelled (Glyco)Sphingolipids
  作者：Patrick Wisse、Henrik Gold、Mina Mirzaian、Maria J. Ferraz、Ginger Lutteke、Richard J. B. H. N. van den Berg、Hans van den Elst、Johan Lugtenburg、Gijsbert A. van der Marel、Johannes M. F. G. Aerts、Jeroen D. C. Codée、Herman S. Overkleeft

  DOI：10.1002/ejoc.201500025

  日期：2015.4

  The synthesis of a focussed library of sphingolipids differing in the number and position of C-13 labels is described. The synthesised sphingolipids differ in substitution at both the sphingosine amine (either palmitoylated or unmodified) and the sphingosine primary hydroxyl (unmodified or glycosylated). Moreover, C-13 atoms are incorporated into either the sphingosine or the palmitate moiety, or both

  描述了在 C-13 标签的数量和位置上不同的鞘脂集中库的合成。合成的鞘脂在鞘氨醇胺（棕榈酰化或未修饰）和鞘氨醇伯羟基（未修饰或糖基化）处的取代不同。此外，C-13 原子被并入鞘氨醇或棕榈酸酯部分或两者中。这组化合物旨在用于相对定量脂质组学研究，以深入了解健康和患病（溶酶体贮积症）患者和动物模型中的鞘脂代谢
• Determination of globotriaosylceramide analogs in the organs of a mouse model of Fabry disease
  作者：Satoshi Ishii、Atsumi Taguchi、Nozomu Okino、Makoto Ito、Hiroki Maruyama

  DOI：10.1074/jbc.ra120.012665

  日期：2020.4

  Fabry disease is a heritable lipid disorder caused by the low activity of ?-galactosidase A and characterized by the systemic accumulation of globotriaosylceramide (Gb3). Recent studies have reported a structural heterogeneity of Gb3 in Fabry disease, including Gb3 isoforms with different fatty acids and Gb3 analogs with modifications on the sphingosine moiety. However, Gb3 assays are often performed only on the selected Gb3 isoforms. To precisely determine the total Gb3 concentration, here we established two methods for determining both Gb3 isoforms and analogs. One was the deacylation method, involving Gb3 treatment with sphingolipid ceramide N-deacylase, followed by an assay of the deacylated products, globotriaosylsphingosine (lyso-Gb3) and its analogs, by ultra-performance LC coupled to tandem MS (UPLC-MS/MS). The other method was a direct assay established in the present study for 37 Gb3 isoforms and analogs/isoforms by UPLC-MS/MS. Gb3s from the organs of symptomatic animals of a Fabry disease mouse model were mainly Gb3 isoforms and two Gb3 analogs, such as Gb3(+18) containing the lyso-Gb3(+18) moiety and Gb3(?2) containing the lyso-Gb3(?2) moiety. The total concentrations and Gb3 analog distributions determined by the two methods were comparable. Gb3(+18) levels were high in the kidneys (24% of total Gb3) and the liver (13%), and we observed Gb3(?2) in the heart (10%) and the kidneys (5%). These results indicate organ-specific expression of Gb3 analogs, insights that may lead to a deeper understanding of the pathophysiology of Fabry disease.
• Qiu, Dongxu; Schmidt, Richard R., Liebigs Annalen der Chemie, 1992, # 3, p. 217 - 224
  作者：Qiu, Dongxu、Schmidt, Richard R.

  DOI：——

  日期：——