(S)-2-(2-Ethenesulfonyl-ethoxycarbonylamino)-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester | 918822-84-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-(2-Ethenesulfonyl-ethoxycarbonylamino)-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-(2-ethenylsulfonylethoxycarbonylamino)-3-(4-hydroxyphenyl)propanoate
• CAS: 918822-84-1
• 化学式: C₁₈H₂₅NO₇S
• 分子量: 399.465
• InChiKey: CFGDGKXNQGHKFQ-HNNXBMFYSA-N

物化性质

• 沸点：
  618.3±55.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-Ethenesulfonyl-ethoxycarbonylamino)-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester 、 苄硫醇 在 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以95%的产率得到(S)-2-[2-(2-Benzylsulfanyl-ethanesulfonyl)-ethoxycarbonylamino]-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester
  参考文献：
  名称：

  A Cleavable Amino−Thiol Linker for Reversible Linking of Amines to DNA

  摘要：

  A cleavable heterobifunctional cross-linker for the reversible conjugation of amines to thiol-modified DNA has been developed and tested. The succinimidyl 2-(vinylsulfonyl)-ethyl carbonate (SVEC) was prepared in three steps and tested for its ability to react with amines and thiols. The linker was efficient for binding leucine to a thiol-modified DNA sequence and for releasing the amino acid at pH 11.8.

  DOI：

  10.1021/jo0619736
• 作为产物：
  描述：

  succinimidyl 2-vinylsulfanylethyl carbonate 在 过氧乙酸 、 碳酸氢钠 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 2.75h， 生成 (S)-2-(2-Ethenesulfonyl-ethoxycarbonylamino)-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester
  参考文献：
  名称：

  A Cleavable Amino−Thiol Linker for Reversible Linking of Amines to DNA

  摘要：

  A cleavable heterobifunctional cross-linker for the reversible conjugation of amines to thiol-modified DNA has been developed and tested. The succinimidyl 2-(vinylsulfonyl)-ethyl carbonate (SVEC) was prepared in three steps and tested for its ability to react with amines and thiols. The linker was efficient for binding leucine to a thiol-modified DNA sequence and for releasing the amino acid at pH 11.8.

  DOI：

  10.1021/jo0619736

文献信息

• A Cleavable Amino−Thiol Linker for Reversible Linking of Amines to DNA
  作者：Jonas W. Højfeldt、Peter Blakskjær, and、Kurt V. Gothelf

  DOI：10.1021/jo0619736

  日期：2006.12.1

  A cleavable heterobifunctional cross-linker for the reversible conjugation of amines to thiol-modified DNA has been developed and tested. The succinimidyl 2-(vinylsulfonyl)-ethyl carbonate (SVEC) was prepared in three steps and tested for its ability to react with amines and thiols. The linker was efficient for binding leucine to a thiol-modified DNA sequence and for releasing the amino acid at pH 11.8.