5-{2-[(5'-oxohexanoyl)amino]ethylamino}carbonylpentyl α-L-rhamnopyranosyl-(1->2)-α-D-glucopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-glucopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-D-glucopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-glucopyranosyl-(1->3)-α-L-rhamnopyranoside | 1384244-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-{2-[(5'-oxohexanoyl)amino]ethylamino}carbonylpentyl α-L-rhamnopyranosyl-(1->2)-α-D-glucopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-glucopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-D-glucopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-glucopyranosyl-(1->3)-α-L-rhamnopyranoside
• 英文别名: N-[2-[6-[(2R,3R,4R,5S,6S)-4-[(2R,3R,4R,5S,6R)-3-acetamido-4-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5S,6S)-4-[(2R,3R,4R,5S,6R)-3-acetamido-4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxyhexanoylamino]ethyl]-5-oxohexanamide
• CAS: 1384244-98-7
• 化学式: C₆₆H₁₁₂N₄O₄₀
• 分子量: 1601.62
• InChiKey: CLKSANYYLMPWDB-UYGMHLPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.6
• 重原子数：
  110
• 可旋转键数：
  34
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  666
• 氢给体数：
  23
• 氢受体数：
  40

反应信息

• 作为产物：
  描述：

  、 5-ketohexanoic acid anhydride 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 5-{2-[(5'-oxohexanoyl)amino]ethylamino}carbonylpentyl α-L-rhamnopyranosyl-(1->2)-α-D-glucopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-glucopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-D-glucopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-glucopyranosyl-(1->3)-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