sodium (2S,3S,4S,5R,6R)-6-(((2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6R)-6-(allyloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate | 1269636-73-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: sodium (2S,3S,4S,5R,6R)-6-(((2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6R)-6-(allyloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate
• CAS: 1269636-73-8
• 化学式: C₂₁H₃₃O₁₇*Na
• 分子量: 580.473
• InChiKey: RFEJJEHDYUUGDD-CIGRHNGZSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -10.6
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  277.58
• 氢给体数：
  9.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  sodium (2S,3S,4S,5R,6R)-6-(((2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6R)-6-(allyloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate 在 4-二甲氨基吡啶 、 乙酸酐 作用下， 反应 28.0h， 生成 allyl (2,4-di-O-acetyl-β-D-glucopyranosylurono-6,3-lactone)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Chemo-bacterial synthesis and immunoreactivity of a brain HNK-1 analogue

  摘要：

  This work reports the synthesis and the biological validation of a trisaccharide analogue of the HNK-1 epitope. The 3-O-sulfo-beta-D-GlcpA-(1 -> 3)-beta-D-Galp-(1 -> 4)-beta-D-Glcp-allyl has been prepared by enzymatic glucuronylation of allyl lactoside by an engineered recombinant Escherichia coli strain followed by a chemoselective sulfation. Subsequent covalent attachment of the ozone-oxidised trisaccharide to bovine serum albumin provided a neo-glycoconjugate, which has been interrogated with antibodies specific to the human natural killer carbohydrate epitope HNK-1. ELISA assays confirmed the absolute requirement of the sulfate group for protein recognition and the potential application of this synthetic oligosaccharide as HNK-1 surrogate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.028