(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate | 1384245-14-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate
• 英文别名: Bn(-3)[Bn(-4)][Bn(-6)]Glc2Ac(a1-3)GlcNAc4Ac6Ac(a1-3)[Bz(-2)][Bn(-4)]Rha(a)-O-C(NH)CCl3；[(2S,3R,4R,5S,6S)-4-[(2R,3R,4R,5S,6R)-3-acetamido-5-acetyloxy-4-[(2S,3R,4S,5R,6R)-3-acetyloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-methyl-5-phenylmethoxy-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 1384245-14-0
• 化学式: C₆₃H₆₉Cl₃N₂O₁₉
• 分子量: 1264.6
• InChiKey: NUOOFYLCGAUYQR-AIKFALTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  87
• 可旋转键数：
  30
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  250
• 氢给体数：
  2
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate 、 5-(methoxycarbonyl)pentyl (2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以60%的产率得到5-(methoxycarbonyl)pentyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthetic Oligosaccharides as Tools to Demonstrate Cross-Reactivity between Polysaccharide Antigens

  摘要：

  Escherichia coli O148 is a nonencapsulated enterotoxigenic (ETEC) Gram negative bacterium that can cause diarrhea, hemorrhagic colt:is, and hemolytic uremic syndrome in humans. The surface-exposed O-specific polysaccharide (O-SP) of the lipopolysaccharide of this bacterium is considered both;l virulence factor and a protective antigen. It is built up of the linear tetrasaccharide repeating unit [3)-alpha-L-Rhap-(1 -> 2)-alpha-D-Glcp-(1 -> 3)-alpha-D-GlcNAcp-(1 -> 3)-alpha-L-Rhap-(1 ->] differing from that of the O-SP of Shigella dysenteriae type 1 (SD) only in that the latter contains a D-Galp residue in place of the glucose moiety of the former. The close similarity of the O-SPs of these bacteria indicated a possible cross-reactivity, To answer this question we synthesized several oligosaccharide fragments of E. coli 0148 O-SP, up to a dodecasaccharide, as well as their bovine serum albumin or recombinant diphtheria toxin conjugates. Immunization of mice with these conjugates induced anti-O-SP-specific serum IgG antibody responses. The antisera reacted equally well with the LPSs of both bacteria, indicating cross-reactivity between the SD and E. coli 0148 O-SPs that was further supported by Western-blot and dot-blot analyses, as well as by inhibition of binding between the antisera and the O-SPs of both bacteria.

  DOI：

  10.1021/jo300299p
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl (3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthetic Oligosaccharides as Tools to Demonstrate Cross-Reactivity between Polysaccharide Antigens

  摘要：

  Escherichia coli O148 is a nonencapsulated enterotoxigenic (ETEC) Gram negative bacterium that can cause diarrhea, hemorrhagic colt:is, and hemolytic uremic syndrome in humans. The surface-exposed O-specific polysaccharide (O-SP) of the lipopolysaccharide of this bacterium is considered both;l virulence factor and a protective antigen. It is built up of the linear tetrasaccharide repeating unit [3)-alpha-L-Rhap-(1 -> 2)-alpha-D-Glcp-(1 -> 3)-alpha-D-GlcNAcp-(1 -> 3)-alpha-L-Rhap-(1 ->] differing from that of the O-SP of Shigella dysenteriae type 1 (SD) only in that the latter contains a D-Galp residue in place of the glucose moiety of the former. The close similarity of the O-SPs of these bacteria indicated a possible cross-reactivity, To answer this question we synthesized several oligosaccharide fragments of E. coli 0148 O-SP, up to a dodecasaccharide, as well as their bovine serum albumin or recombinant diphtheria toxin conjugates. Immunization of mice with these conjugates induced anti-O-SP-specific serum IgG antibody responses. The antisera reacted equally well with the LPSs of both bacteria, indicating cross-reactivity between the SD and E. coli 0148 O-SPs that was further supported by Western-blot and dot-blot analyses, as well as by inhibition of binding between the antisera and the O-SPs of both bacteria.

  DOI：

  10.1021/jo300299p