3-(2-(vinylsulfonyl)ethoxy)prop-1-yne

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 3-(2-(vinylsulfonyl)ethoxy)prop-1-yne
• 英文别名: 3-(2-Ethenylsulfonylethoxy)prop-1-yne；3-(2-ethenylsulfonylethoxy)prop-1-yne
• 化学式: C₇H₁₀O₃S
• 分子量: 174.221
• InChiKey: ROIOTCGEKQFQEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-(vinylsulfonyl)ethoxy)prop-1-yne 、 3-叠氮基-7-(二乙氨基)香豆素 在 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以37%的产率得到7-(diethylamino)-3-(4-((2-(vinylsulfonyl)ethoxy)methyl)-1H-1,2,3-triazol-1-yl)-coumarin
  参考文献：
  名称：

  Fluorogenic tagging of peptides via Cys residues using thiol-specific vinyl sulfone affinity tags

  摘要：

  Fluorescent tagging of Cys-containing peptides is presented herein. The procedure follows a two-step sequential reaction scheme using thiol specific bifunctional chemical reporters and fluorogenic labels. Vinyl-sulfone bearing chemical reporters have been synthesized and demonstrated to selectively modify cysteine under physiological conditions in the presence of other nucleophilic amino acids. Bifunctional chemical reporters decorated with a terminal alkyne moiety, suitable for modification with azide containing fluorogenic labels were also synthesized. Such fluorogenic (turn on) labels in combination with these new vinyl-sulfone tags can be used generally in fluorescent modulation schemes of thiol-bearing biomolecules. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.103
• 作为产物：
  描述：

  二乙烯基砜 、 2-丙炔-1-醇 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以49%的产率得到3-(2-(vinylsulfonyl)ethoxy)prop-1-yne
  参考文献：
  名称：

  Fluorogenic tagging of peptides via Cys residues using thiol-specific vinyl sulfone affinity tags

  摘要：

  Fluorescent tagging of Cys-containing peptides is presented herein. The procedure follows a two-step sequential reaction scheme using thiol specific bifunctional chemical reporters and fluorogenic labels. Vinyl-sulfone bearing chemical reporters have been synthesized and demonstrated to selectively modify cysteine under physiological conditions in the presence of other nucleophilic amino acids. Bifunctional chemical reporters decorated with a terminal alkyne moiety, suitable for modification with azide containing fluorogenic labels were also synthesized. Such fluorogenic (turn on) labels in combination with these new vinyl-sulfone tags can be used generally in fluorescent modulation schemes of thiol-bearing biomolecules. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.103

文献信息

• Fluorogenic tagging of peptides via Cys residues using thiol-specific vinyl sulfone affinity tags
  作者：Gergely B. Cserép、Zsuzsa Baranyai、Dávid Komáromy、Kata Horváti、Szilvia Bősze、Péter Kele

  DOI：10.1016/j.tet.2014.05.103

  日期：2014.9

  Fluorescent tagging of Cys-containing peptides is presented herein. The procedure follows a two-step sequential reaction scheme using thiol specific bifunctional chemical reporters and fluorogenic labels. Vinyl-sulfone bearing chemical reporters have been synthesized and demonstrated to selectively modify cysteine under physiological conditions in the presence of other nucleophilic amino acids. Bifunctional chemical reporters decorated with a terminal alkyne moiety, suitable for modification with azide containing fluorogenic labels were also synthesized. Such fluorogenic (turn on) labels in combination with these new vinyl-sulfone tags can be used generally in fluorescent modulation schemes of thiol-bearing biomolecules. (C) 2014 Elsevier Ltd. All rights reserved.