S-D-biotinoyl-4-aminobenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose | 325470-02-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: S-D-biotinoyl-4-aminobenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose
• CAS: 325470-02-8
• 化学式: C₃₁H₄₂N₄O₁₀S₂
• 分子量: 694.827
• InChiKey: FZUDBJYRVRVWNT-DQUNXBDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  187.46
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  S-D-biotinoyl-4-aminobenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以56%的产率得到S-D-biotinoyl-4-aminobenzyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  The synthesis of biotinylated carbohydrates as probes for carbohydrate-recognizing proteins

  摘要：

  The intimate involvement of carbohydrate-protein interactions in a number of important biological processes has prompted several research efforts towards developing new met:hods of investigating these glycobiological interactions. Biotinylated oligosaccharides are emerging as a new and powerful tool in this area of research, primarily due to their high affinity towards streptavidin and their ease of immobilization on matrices. Here we describe a novel synthetic approach towards biotinylated saccharides which incorporate a UV absorbing group into the final compounds. The synthetic strategy described is applicable to a variety of saccharides, with examples of biotinylated mono-, di-, and trisaccharides being prepared with overall high efficiency. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00201-7
• 作为产物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-1-S-acetyl-2-deoxy-1-thio-β-D-glucopyranose 在 乙酸肼 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 tin(ll) chloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 S-D-biotinoyl-4-aminobenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose
  参考文献：
  名称：

  The synthesis of biotinylated carbohydrates as probes for carbohydrate-recognizing proteins

  摘要：

  The intimate involvement of carbohydrate-protein interactions in a number of important biological processes has prompted several research efforts towards developing new met:hods of investigating these glycobiological interactions. Biotinylated oligosaccharides are emerging as a new and powerful tool in this area of research, primarily due to their high affinity towards streptavidin and their ease of immobilization on matrices. Here we describe a novel synthetic approach towards biotinylated saccharides which incorporate a UV absorbing group into the final compounds. The synthetic strategy described is applicable to a variety of saccharides, with examples of biotinylated mono-, di-, and trisaccharides being prepared with overall high efficiency. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00201-7