3,4,6-tri-O-acetyl-2-(4,5-dichlorophthalimido)-2-deoxy-D-glucopyranosyl bromide | 1036637-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-(4,5-dichlorophthalimido)-2-deoxy-D-glucopyranosyl bromide
• 英文别名: [(2R,3S,4R,5R)-3,4-diacetyloxy-6-bromo-5-(5,6-dichloro-1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl acetate
• CAS: 1036637-16-7
• 化学式: C₂₀H₁₈BrCl₂NO₉
• 分子量: 567.174
• InChiKey: QQWUDGNGALWTNG-XNIMBYMISA-N

物化性质

• 沸点：
  629.2±55.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-(4,5-dichlorophthalimido)-2-deoxy-D-glucopyranosyl bromide 、 2-azidododecanol 在 2,4,6-三甲基吡啶 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  IMMUNITY INDUCER FOR SACCHARIDE ANTIGENS

  摘要：

  本发明提供了一种免疫诱导剂和使用该免疫诱导剂的免疫诱导方法。该免疫诱导剂对任何目标寡糖抗原具有免疫增强效果，特别是对哺乳动物来源的糖蛋白N-连接糖链中包含的寡糖抗原具有免疫增强效果；能够提供具有高特异性和亲和力的单克隆抗体以及有效成分为包括目标寡糖抗原（R）的糖脂，由通式（2）表示，或其盐。通式（2）：R—Z—Y—CH（NH—CO—（CH2）n1—CH3）—（CH2）n2—CH3（在公式中，R表示由至少一种单糖组成的直链或支链寡糖，包括2-30个单糖。Z表示单键，O，S或NH，与硫甲基化，氨基甲基化糖醇结合的连接物。Y表示—（CH2）m—。n1表示2-40的整数，n2表示1-27的整数，m表示1-30的整数）。

  公开号：

  US20160074522A1

文献信息

• Chemical and enzymatic synthesis of neoglycolipids in the presence of cyclodextrins
  作者：Izuru Nagashima、Hiroki Shimizu、Takahiko Matsushita、Shin-Ichiro Nishimura

  DOI：10.1016/j.tetlet.2008.03.103

  日期：2008.5

  The efficiency of cyclodextrins (CDs), alpha-CD, beta-CD and gamma-CD, for the blotting of hydrophobic substrates to water-soluble polymers and for the synthesis of neoglycolipids using glycosyltransferase is described. CDs did not disturb HPLC purification and did not bring lather. These merits are superior to surfactants commonly used in such a case. The utility of CDs as a novel and efficient supporting material for enzymatic glycosylation is also discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• Chemical Synthesis, Folding, and Structural Insights into <i>O</i>-Fucosylated Epidermal Growth Factor-like Repeat 12 of Mouse Notch-1 Receptor
  作者：Kazumi Hiruma-Shimizu、Kensaku Hosoguchi、Yan Liu、Naoki Fujitani、Takashi Ohta、Hiroshi Hinou、Takahiko Matsushita、Hiroki Shimizu、Ten Feizi、Shin-Ichiro Nishimura

  DOI：10.1021/ja105216u

  日期：2010.10.27

  Notch receptors are cell surface glycoproteins that play key roles in a number of developmental cascades in metazoa. The extracellular domains of Notch-1 receptors are composed of 36 tandem epidermal growth factor (EGF)-like repeats, many of which are modified at highly conserved consensus sites by an unusual form of O-glycan, with O-fucose. The O-fucose residues on certain EGF repeats may be elongated. In mammalian cells this can be a tetrasaccharide, Siaα2,3Galβ1,4GlcNAcβ1,3Fucα1→. This elongation process is initiated by the action of O-fucose-specific β1,3 N-acetylglucosaminyltransferases of the Fringe family. There is evidence that the addition of GlcNAc by Fringe serves as an essential modulator of the interaction of Notch with its ligands and the triggering of activation. Here we describe the efficient synthesis, folding, and structural characterization of EGF repeat 12 (EGF 12) of a mouse Notch-1 receptor bearing different O-fucose glycan chains. We demonstrate that the three disulfide bonds, Cys(456)-Cys(467) (C1-C3), Cys(461)-Cys(476) (C2-C4), and Cys(478)-Cys(487) (C5-C6) were correctly formed in the nonglycosylated as well as the O-fucosylated forms of EGF 12. Three-dimensional structural studies by NMR reveal that the methyl group of fucose is in close contact with ILe(475), Met(477), Pro(478) residues and this stabilizes the conformation of the antiparallel β-sheet of EGF 12. The addition of the GlcNAc residue on O-fucosylated EGF 12 induces a significant conformational change in the adjacent tripeptide sequence, Gln(462)Asn(463)Asp(464), which is a motif involved in the natural, enzymatic O-fucosylation at the conserved site (Cys(461)X(4)Ser/ThrCys(467)).