acetyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α/β-D-galactopyranoside | 80446-82-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α/β-D-galactopyranoside
• 英文别名: 1,2,3,6-Tetra-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-α/β-D-galactopyranose；O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-D-galactopyranoside；Gal2Ac3Ac4Ac6Ac(a1-4)Gal1Ac2Ac3Ac6Ac；[(2R,3S,4S,5R)-4,5,6-triacetyloxy-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 80446-82-8
• 化学式: C₂₈H₃₈O₁₉
• 分子量: 678.598
• InChiKey: WOTQVEKSRLZRSX-FRVWXVAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  acetyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α/β-D-galactopyranoside 在 2,4,6-三甲基吡啶 、 氢溴酸 、 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 2-(p-aminophenylthio)ethyl 4-O-α-D-galactopyranosyl-β-D-galactopyranoside
  参考文献：
  名称：

  Preparation and applications of 2-bromoethyl glycosides: synthesis of spacer-arm glycosides and agglutination inhibitors

  摘要：

  DOI：

  10.1016/0008-6215(82)85020-9
• 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 生成 acetyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α/β-D-galactopyranoside
  参考文献：
  名称：

  JANSSON, KARL;AHLFORS, STEFAN;FREJD, TORBJORN;KIHLBERG, JAN;MAGNUSSON, GO+, J. ORG. CHEM., 53,(1988) N 24, C. 5629-5647

  摘要：

  DOI：

文献信息

• Capture of Uropathogenic<i>E. coli</i>by Using Synthetic Glycan Ligands Specific for the Pap-Pilus
  作者：Hailemichael O. Yosief、Alison A. Weiss、Suri S. Iyer

  DOI：10.1002/cbic.201200582

  日期：2013.1.21

  Synthetic glycoconjugates for capturing pathogens: Mono‐ and biantennary biotinylated glycoconjugates have been synthesized, and their ability to capture different E. coli strains (see graph) indicates that these molecules could be used to differentiate between different E. coli pathovars.

  用于捕获病原体的合成糖缀合物：已经合成了单天线和双天线生物素化糖缀合物，它们捕获不同大肠杆菌菌株的能力（见图）表明这些分子可用于区分不同的大肠杆菌病原体。
• Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and ‘click’ conjugation
  作者：Hilbert M. Branderhorst、Raymond Kooij、Annika Salminen、Lieneke H. Jongeneel、Christopher J. Arnusch、Rob M. J. Liskamp、Jukka Finne、Roland J. Pieters

  DOI：10.1039/b800283e

  日期：——

  A galabiose disaccharide building block was synthesized by an efficient pectinase cleavage of polygalacturonic acid and subsequent chemical functional group transformations. Besides the disaccharide, the corresponding trisaccharide was also obtained and modified. The compounds were subsequently conjugated to dendrimers with up to eight end groups using 'click' chemistry. The compounds were evaluated

  通过聚半乳糖醛酸的有效果胶酶切割和随后的化学官能团转化合成了半乳糖二糖结构单元。除了二糖以外，还获得并改性了相应的三糖。随后使用“点击”化学将化合物缀合至具有最多八个端基的树枝状聚合物。在血凝测定中，将这些化合物评估为病原体猪链球菌粘附的抑制剂，并且对四价和八价半乳糖酶化合物的MIC值均在低纳摩尔范围内观察到了强抑制作用。相应的八价三糖为约。抑制剂弱20倍。
• 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.
• Probing of the combining site of the PapG adhesin of uropathogenic Escherichia coli bacteria by synthetic analogs of galabiose
  作者：Jan Kihlberg、Scott J. Hultgren、Staffan Normark、Goeran Magnusson

  DOI：10.1021/ja00198a056

  日期：1989.8