2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-trichloroacetamidato-α-D-galactopyranosyl trichloroacetimidate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-trichloroacetamidato-α-D-galactopyranosyl trichloroacetimidate
• 英文别名: [(4aR,6R,7R,8R,8aR)-7-acetamido-2-phenyl-6-(2,2,2-trichloroethanimidoyl)oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2,2,2-trichloroethanimidate
• 化学式: C₁₉H₁₉Cl₆N₃O₆
• 分子量: 598.094
• InChiKey: AAOQAFHNALRZCD-BXKJZEQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-trichloroacetamidato-α-D-galactopyranosyl trichloroacetimidate 在 4 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 、 氰化汞 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 22.0h， 生成 2-azidoethyl (β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Investigation of Nonspecific Effects of Different Dyes in the Screening of Labeled Carbohydrates against Immobilized Proteins

  摘要：

  Carbohydrates play an important role in life processes, and combinatorial chemistry can provide useful sources of thousands of synthetic carbohydrates as potential ligands for biological receptors. To accelerate the detection of positive hits arising from specific interactions between a carbohydrate and a protein, the use of fluorescent dyes can serve as a reliable detecting tool. A study of labeled carbohydrates to lectins conjugated to a solid-support shows that succinimidyl 6-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)hexanoate (NBD-X) dye provides by far the lowest level of nonspecific interaction with immobilized protein. This observation is in stark contrast with the commonly used labeling reagents constituted of charged and aromatic groups, for instance, FITC and TAMRA dyes.

  DOI：

  10.1021/jo051503w
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-D-吡喃半乳糖 在 4 A molecular sieve 、 camphor-10-sulfonic acid 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-trichloroacetamidato-α-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Investigation of Nonspecific Effects of Different Dyes in the Screening of Labeled Carbohydrates against Immobilized Proteins

  摘要：

  Carbohydrates play an important role in life processes, and combinatorial chemistry can provide useful sources of thousands of synthetic carbohydrates as potential ligands for biological receptors. To accelerate the detection of positive hits arising from specific interactions between a carbohydrate and a protein, the use of fluorescent dyes can serve as a reliable detecting tool. A study of labeled carbohydrates to lectins conjugated to a solid-support shows that succinimidyl 6-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)hexanoate (NBD-X) dye provides by far the lowest level of nonspecific interaction with immobilized protein. This observation is in stark contrast with the commonly used labeling reagents constituted of charged and aromatic groups, for instance, FITC and TAMRA dyes.

  DOI：

  10.1021/jo051503w

文献信息

• Investigation of Nonspecific Effects of Different Dyes in the Screening of Labeled Carbohydrates against Immobilized Proteins
  作者：Meenakshi Dowlut、Dennis G. Hall、Ole Hindsgaul

  DOI：10.1021/jo051503w

  日期：2005.11.1

  Carbohydrates play an important role in life processes, and combinatorial chemistry can provide useful sources of thousands of synthetic carbohydrates as potential ligands for biological receptors. To accelerate the detection of positive hits arising from specific interactions between a carbohydrate and a protein, the use of fluorescent dyes can serve as a reliable detecting tool. A study of labeled carbohydrates to lectins conjugated to a solid-support shows that succinimidyl 6-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)hexanoate (NBD-X) dye provides by far the lowest level of nonspecific interaction with immobilized protein. This observation is in stark contrast with the commonly used labeling reagents constituted of charged and aromatic groups, for instance, FITC and TAMRA dyes.