O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate | 192770-25-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate
• CAS: 192770-25-5
• 化学式: C₂₈H₃₆Cl₃NO₁₈
• 分子量: 780.949
• InChiKey: QUJSSIATSJUBGC-PQYWDRMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  50.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  244.87
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (2R,3R,4S,5R,6R)-2-((2R,3R,4R,5R,6S)-6-Benzylsulfanyl-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Synthesis of some divalent O- and S-glycosides of galabiose and globotriose

  摘要：

  Derivatives of galabiose (alpha-D-Galp-(1-->4)-D-Galp) and globotriose (alpha-D-Galp-(1-->4)-beta-D-Galp(1-->4)-D-Glcp) were coupled to various 1,2- and 1,3-dihydroxymethyl- and dimercaptomethylbenzenes to give the corresponding divalent glycosides, potentially useful as inhibitors of bacterial adhesion. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00021-4
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranoside 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 1.33h， 生成 O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Di-, Tri-, and Tetravalent Dendritic Galabiosides That Inhibit Hemagglutination by Streptococcus suis at Nanomolar Concentration

  摘要：

  Galabiose (Gal alpha 1-4Gal) derivatives were coupled to carrier molecules having mono-, di-, tri-, and tetrameric functionalities, thus creating mono- to tetravalent dendritic galabiosides (1-9). The di- to tetravalent galabiosides were several hundred times more efficient than the monomeric galabiosides in inhibiting hemagglutination by the Gram-positive bacterium Streptococcus suis, resulting in complete inhibition at low nanomolar concentrations. This is unprecedented in the field of inhibition of bacterial adhesion by soluble compounds.

  DOI：

  10.1021/ja970859p

文献信息

• Synthesis of polyanionic glycopolymers for the facile assembly of glycosyl arrays
  作者：Hirotaka Uzawa、Hiroki Ito、Masayuki Izumi、Hideo Tokuhisa、Kazuhiro Taguchi、Norihiko Minoura

  DOI：10.1016/j.tet.2005.03.102

  日期：2005.6

  Polyanionic glycopolymers were synthesized aiming at establishing a simple process for assembling glycosyl arrays. The synthetic glycopolymers carry the key carbohydrate epitopes of alpha-D-galactobioside (Gb(2)), beta-lactoside, and U-D-mannopyranoside, each of which serves as a ligand of bacterial toxins and adhesion proteins. The Gb(2) epitope, prepared from penta-O-acetyl-D-galactopyranose, was coupled with poly(ethylene-alt-maleic anhydride) in a polymer reaction to afford a Gb(2)-embedded glycopolymer having also carboxylate (COO-) polyanions at the side chain. The polyanionic glycopolymer was then applied to a preparation of sugar-coated gold electrodes, which involves an alternating layer-by-layer adsorption based on electrostatic interactions. The presence of the Gb(2)-Coat on the surface was evidenced by Fourier transform infrared reflection absorption spectroscopy. The Gb(2)-coated glyco-chip was stable in 10 mM HEPES buffer containing 150 mM NaCl aq. Other glycopolymers carrying the beta-lactoside and alpha-D-mannopyranoside epitopes were applied to the same assembling process. The derived glycosyl arrays will be useful for detecting Shiga toxins, other pathogenic toxins and viruses when applied as glyco-chips for surface plasmon resonance or quartz crystal microbalance technique. (c) 2005 Elsevier Ltd. All rights reserved.