2-[2-[2-(2-biotinylaminoethoxy)ethoxy]ethoxy]-4-[3-(trifluoromethyl)-3H-diazirine-3-yl]benzyloxyphthalimide | 299931-17-2

• 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: 2-[2-[2-(2-biotinylaminoethoxy)ethoxy]ethoxy]-4-[3-(trifluoromethyl)-3H-diazirine-3-yl]benzyloxyphthalimide
• CAS: 299931-17-2
• 化学式: C₃₃H₃₇F₃N₆O₈S
• 分子量: 734.753
• InChiKey: GAZOTBPONRIADL-MPYJOUPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  51.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  169.25
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-[2-[2-(2-biotinylaminoethoxy)ethoxy]ethoxy]-4-[3-(trifluoromethyl)-3H-diazirine-3-yl]benzyloxyphthalimide 在 N,N-二异丙基乙胺 、 肼 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  One-Step Synthesis of Biotinyl Photoprobes from Unprotected Carbohydrates

  摘要：

  A simple and versatile approach for the preparation of carbohydrate photoprobes has been developed. By a single-step reaction at 37 degrees C, a biotinylated carbene-generating unit was introduced to the reducing end of unprotected carbohydrates. Micromole quantities of N-acetyllactosamine, Lewis X trisaccharide, and sialyl Lewis X tetrasaccharide were easily converted to their biotinylated photoreactive analogues, which enabled the nonradioisotopic chemiluminescent detection of the photolabeled products. Thus, a sequence of lectin photoaffinity labeling, from the probe synthesis to the detection of labeled protein, was readily accomplished within one week. Our strategy may be applicable to any aldehyde-bearing ligand.

  DOI：

  10.1021/jo000414a
• 作为产物：
  描述：

  (+)生物素-N-琥珀酰亚胺基酯 、 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以320 mg的产率得到2-[2-[2-(2-biotinylaminoethoxy)ethoxy]ethoxy]-4-[3-(trifluoromethyl)-3H-diazirine-3-yl]benzyloxyphthalimide
  参考文献：
  名称：

  One-Step Synthesis of Biotinyl Photoprobes from Unprotected Carbohydrates

  摘要：

  A simple and versatile approach for the preparation of carbohydrate photoprobes has been developed. By a single-step reaction at 37 degrees C, a biotinylated carbene-generating unit was introduced to the reducing end of unprotected carbohydrates. Micromole quantities of N-acetyllactosamine, Lewis X trisaccharide, and sialyl Lewis X tetrasaccharide were easily converted to their biotinylated photoreactive analogues, which enabled the nonradioisotopic chemiluminescent detection of the photolabeled products. Thus, a sequence of lectin photoaffinity labeling, from the probe synthesis to the detection of labeled protein, was readily accomplished within one week. Our strategy may be applicable to any aldehyde-bearing ligand.

  DOI：

  10.1021/jo000414a

文献信息

• Phenyldiazirine compounds and photoaffinity labeling reagent
  申请人：Hatanaka Yasumaru

  公开号：US06903223B1

  公开（公告）日：2005-06-07

  This invention offers a photoreactive labeling reagent consisting of a novel biotinylated phenyldiazirine compound; a photoaffinity labeling reagent consisting of a saccharide-linked biotinylated phenyldiazirine compound where a saccharide compound is introduced into the novel compound; and a novel diazirine compound for such a reagent. The invention covers a biotinylated phenyldiazirine compound of the following formula (II); a phenyldiazirine compound which is an intermediate for synthesizing the above; a saccharide-linked biotinylated phenyldiazirine compound derived from the compound of the formula (II) and a saccharide compound and a method for manufacturing the same; a photoreactive labeling reagent containing the compound of the formula (II); a photoaffinity labeling reagent containing the saccharide-linked biotinylated phenyldiazirine compound; and a method for labeling a saccharide receptor using the reagent.

  这项发明提供了一种光反应性标记试剂，包括一种新型生物素化苯基重氮化合物；一种光亲和标记试剂，包括一种糖链连接的生物素化苯基重氮化合物，其中将糖类化合物引入到该新型化合物中；以及用于该试剂的一种新型重氮化合物。该发明涵盖以下化学式（II）的生物素化苯基重氮化合物；一种用于合成上述化合物的中间体苯基重氮化合物；从化学式（II）的化合物和糖类化合物衍生的糖链连接的生物素化苯基重氮化合物及其制造方法；包含化学式（II）的化合物的光反应性标记试剂；包含糖链连接的生物素化苯基重氮化合物的光亲和标记试剂；以及使用该试剂标记糖类受体的方法。