allyl (methyl 2,4-di-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 1269636-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl (methyl 2,4-di-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 1269636-75-0
• 化学式: C₃₈H₅₂O₂₅
• 分子量: 908.816
• InChiKey: BZOWMRTYGLTVSD-OLFBFEIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.62
• 重原子数：
  63.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  312.31
• 氢给体数：
  1.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  allyl (methyl 2,4-di-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 三氧化硫吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.33h， 以64%的产率得到
  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
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 sodium acetate 作用下， 反应 26.0h， 生成 allyl (methyl 2,4-di-O-acetyl-β-D-glucopyranosyluronate)-(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