1-βD-galactosyl-N-(cis-15-tetracosenoyl)-(4E)-sphingenine | 17283-91-9

• 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: 1-βD-galactosyl-N-(cis-15-tetracosenoyl)-(4E)-sphingenine
• 英文别名: (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(15(Z)-tetracosenoylamino)-3-hydroxyoctadec-4-ene；N-Nervonylgalactocerebroside；N-((1S,2R)-1-β-D-galactopyranosyloximethyl-2-hydroxy-heptadec-3t-enyl)-tetracos-15c-enamide；N-((1S,2R)-1-β-D-Galactopyranosyloxymethyl-2-hydroxy-heptadec-3t-enyl)-tetracos-15c-enamid；GalCer(d18:1/24:1(15Z))；(Z)-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]tetracos-15-enamide
• CAS: 17283-91-9
• 化学式: C₄₈H₉₁NO₈
• 分子量: 810.252
• InChiKey: WBOZIXHPUPAOIA-JMDWBTAUSA-N

物化性质

• 沸点：
  902.3±65.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  57
• 可旋转键数：
  40
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  8

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  1-βD-galactosyl-N-(cis-15-tetracosenoyl)-(4E)-sphingenine 在 二正丁基氧化锡 、 三甲基铵三氧化硫共聚物 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 反应 8.0h， 以95%的产率得到(2S,3R,4E)-1-[3-O-(sodium oxysulfonyl)-β-D-galactopyranosyloxy]-2-(15(Z)-tetracosenoylamino)-3-hydroxyoctadec-4-ene
  参考文献：
  名称：

  [EN] GLYCOLIPIDS AND ANALOGUES THEREOF AS ANTIGENS FOR NK T CELLS
  [FR] GLYCOLIPIDES ET ANALOGUES ASSOCIES UTILISES EN TANT QU'ANTIGENES DES LYMPHOCYTES NKT

  摘要：

  公开号：

  WO2006071848A3
• 作为产物：
  描述：

  神经酸 、 神经鞘氨醇半乳糖苷 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以64%的产率得到1-βD-galactosyl-N-(cis-15-tetracosenoyl)-(4E)-sphingenine
  参考文献：
  名称：

  CD1a-binding glycosphingolipids stimulating human autoreactive T-cells: synthesis of a family of sulfatides differing in the acyl chain moiety

  摘要：

  Native sulfatide (a mixture of 3-sulfated beta-D-galactopyranosylceramides with different fatty acids at the ceramide moiety) is an antigen presented by CD1a proteins. Herein the preparation of four sulfatides, which are constituents of the natural mixture and bear palmitic, stearic, behenic or nervonic fatty acid chains, is described. Azidosphingosine was stereoselectively synthesized through a CuCN-catalyzed allylic alkylation of a hexenitol dimesylate derived from D-xylose; beta-glycosylation of azidosphingosine, with a suitable D-galactosyl trichloroacetimidate led, after reduction of the azido, group, to the galactosylsphingosine skeleton, which was derivatized with the different fatty acids. Final regioselective 3-sulfation gave the desired sulfatides, which were tested for activation of sulfatide-specific and CD1a-restricted T-cell clones. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01092-x

文献信息

• Dibutylstannylene acetals: Useful intermediates for the regioselective sulfation of glycosides.
  作者：Bénédicte Guilbert、Nicola J. Davis、Melanie Pearce、Robin T. Aplin、Sabine L. Flitsch

  DOI：10.1016/s0957-4166(00)86292-8

  日期：1994.11

  Sulfated mono- and disaccharides were synthesised by a novel sulfation method via regioselective activation of the saccharides to their dibutyltin stannylene acetals, followed by treatment with sulfur trioxidetrimethylamine. This methodology was applied to the synthesis of 3′-sulfated lactosides 15 and 23, galactosylceramide sulfatide 3 and 2′-sulfated maltosides 30, 32 and 34.

  硫酸化的单-和二糖是由一种新的硫酸化的方法合成经由糖类它们二丁基锡stannylene缩醛的区域选择性活化，随后用硫trioxidetrimethylamine治疗。该方法学应用于3'-硫酸化的乳糖苷15和23，半乳糖基神经酰胺硫化物3和2'-硫酸化的麦芽糖苷30、32和34的合成。
• Liquid secondary ionization, tandem and matrix-assisted laser desorption/ionization time-of-flight mass spectrometric characterization of glycosphingolipid derivatives
  作者：Hélène Perreault、Catherine E. Costello

  DOI：10.1002/oms.1210291205

  日期：1994.12

  AbstractPermethylated, peracetylated and perbenzoylated derivatives of glycosphingolipids (GSLs) were prepared to compare their liquid secondary ionization mass spectrometric (LSIMS) and collision‐induced dissociation tandem mass spectrometric (CID/MS/MS) fragmentation patterns and also to determine sensitivity improvement in LSIMS and matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry (MALDI‐TOFMS) relative to the native species. Permethylation was carried out in the liquid phase, whereas peracetylation and perbenzoylation could be effected using either liquid (bulk)‐phase or gas‐phase procedures. Lower amounts of starting material were required for the gas‐phase derivatization (⩽ 100 pmol) compared with the bulk phase (⩽1 nmol), because the former method permits more efficient sample handling. All three types of derivatives yielded sensitivity improvements of at least two orders of magnitude over the native species in both LSIMS and MALDI‐TOFMS. The behavior of the permethylated compounds was used as the benchmark for GSL structural information content in normal and tandem mass spectra. Fragments present in spectra of the three types of derivatives generated complementary information. Permethylated GSLs favored the formation of ions related to the ceramide moieties, whereas peracetylation enhanced the production of carbohydrate‐related ions. The LSI mass spectra of perbenzoylated GSLs contained information on both ceramide and sugar portions of the molecules. Each of the LSIMS, MS/MS and MALDI‐TOFMS techniques proved to be complementary to the others in this study; the use of all three is recommended for the generation of complete structural information.
• [EN] GLYCOLIPIDS AND ANALOGUES THEREOF AS ANTIGENS FOR NK T CELLS<br/>[FR] GLYCOLIPIDES ET ANALOGUES ASSOCIES UTILISES EN TANT QU'ANTIGENES DES LYMPHOCYTES NKT
  申请人：UNIV ROCKEFELLER

  公开号：WO2006071848A3

  公开（公告）日：2006-09-14
• CD1a-binding glycosphingolipids stimulating human autoreactive T-cells: synthesis of a family of sulfatides differing in the acyl chain moiety
  作者：Federica Compostella、Laura Franchini、Gennaro De Libero、Giovanni Palmisano、Fiamma Ronchetti、Luigi Panza

  DOI：10.1016/s0040-4020(02)01092-x

  日期：2002.10

  Native sulfatide (a mixture of 3-sulfated beta-D-galactopyranosylceramides with different fatty acids at the ceramide moiety) is an antigen presented by CD1a proteins. Herein the preparation of four sulfatides, which are constituents of the natural mixture and bear palmitic, stearic, behenic or nervonic fatty acid chains, is described. Azidosphingosine was stereoselectively synthesized through a CuCN-catalyzed allylic alkylation of a hexenitol dimesylate derived from D-xylose; beta-glycosylation of azidosphingosine, with a suitable D-galactosyl trichloroacetimidate led, after reduction of the azido, group, to the galactosylsphingosine skeleton, which was derivatized with the different fatty acids. Final regioselective 3-sulfation gave the desired sulfatides, which were tested for activation of sulfatide-specific and CD1a-restricted T-cell clones. (C) 2002 Elsevier Science Ltd. All rights reserved.