2-(6-tert-butoxycarbonylmethoxy-3-oxo-3H-xanthen-9-yl)-4-(2-{[2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethylcarbamoyl]-methoxy}-acetylamino)-benzoic acid ethyl ester | 886053-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(6-tert-butoxycarbonylmethoxy-3-oxo-3H-xanthen-9-yl)-4-(2-{[2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethylcarbamoyl]-methoxy}-acetylamino)-benzoic acid ethyl ester
• 英文别名: ethyl 4-[[2-[2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethylamino]-2-oxoethoxy]acetyl]amino]-2-[3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]-6-oxoxanthen-9-yl]benzoate
• CAS: 886053-31-2
• 化学式: C₄₉H₄₇N₃O₁₂
• 分子量: 869.925
• InChiKey: RTLKFTRSLXOICT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  64
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  194
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-(6-tert-butoxycarbonylmethoxy-3-oxo-3H-xanthen-9-yl)-4-(2-{[2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethylcarbamoyl]-methoxy}-acetylamino)-benzoic acid ethyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到2-(6-carboxymethoxy-3-oxo-3H-xanthen-9-yl)-4-(2-{[2-(9H-fluoren-9-ylmethoxycarbonyl-amino)-ethylcarbamoyl]-methoxy}-acetylamino)-benzoic acid ethyl ester
  参考文献：
  名称：

  Fluorescein-based amino acids for solid phase synthesis of fluorogenic protease substrates

  摘要：

  An efficient synthesis of new type fluorescent amino acids is described. The Fmoc-protected dyes can be prepared in a four-step procedure with similar to 30% overall yield from aminofluoresceins and other inexpensive commercially available precursors. The dyes are much more photostable compared to fluorescein and exhibit constant pH-independent fluorescence that is advantageous in biological applications. The Fmoc-protected fluorescent amino acids are ready for use in solid phase peptide synthesis. As a proof of concept, a fluorogenic papain Substrate was synthesized and employed for on-bead detection of the protease activity. By using a novel technique for quantitative analysis of bead fluorescence, a similar to 2.7-fold increase in mean bead brightness was measured and was attributed to Substrate cleavage by papain. The new type fluorescent amino acids seem to be a promising tool for the synthesis of fluorescent peptide ligands and fluorogenic protease substrates. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.037
• 作为产物：
  描述：

  4-amino-2-(6-tert-butoxycarbonylmethoxy-3-oxo-3H-xanthen-9-yl)-benzoic acid ethyl ester 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(6-tert-butoxycarbonylmethoxy-3-oxo-3H-xanthen-9-yl)-4-(2-{[2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethylcarbamoyl]-methoxy}-acetylamino)-benzoic acid ethyl ester
  参考文献：
  名称：

  Fluorescein-based amino acids for solid phase synthesis of fluorogenic protease substrates

  摘要：

  An efficient synthesis of new type fluorescent amino acids is described. The Fmoc-protected dyes can be prepared in a four-step procedure with similar to 30% overall yield from aminofluoresceins and other inexpensive commercially available precursors. The dyes are much more photostable compared to fluorescein and exhibit constant pH-independent fluorescence that is advantageous in biological applications. The Fmoc-protected fluorescent amino acids are ready for use in solid phase peptide synthesis. As a proof of concept, a fluorogenic papain Substrate was synthesized and employed for on-bead detection of the protease activity. By using a novel technique for quantitative analysis of bead fluorescence, a similar to 2.7-fold increase in mean bead brightness was measured and was attributed to Substrate cleavage by papain. The new type fluorescent amino acids seem to be a promising tool for the synthesis of fluorescent peptide ligands and fluorogenic protease substrates. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.037

文献信息

• Fluorescein-based amino acids for solid phase synthesis of fluorogenic protease substrates
  作者：Olga N. Burchak、Laurent Mugherli、François Chatelain、Maxim Y. Balakirev

  DOI：10.1016/j.bmc.2005.11.037

  日期：2006.4

  An efficient synthesis of new type fluorescent amino acids is described. The Fmoc-protected dyes can be prepared in a four-step procedure with similar to 30% overall yield from aminofluoresceins and other inexpensive commercially available precursors. The dyes are much more photostable compared to fluorescein and exhibit constant pH-independent fluorescence that is advantageous in biological applications. The Fmoc-protected fluorescent amino acids are ready for use in solid phase peptide synthesis. As a proof of concept, a fluorogenic papain Substrate was synthesized and employed for on-bead detection of the protease activity. By using a novel technique for quantitative analysis of bead fluorescence, a similar to 2.7-fold increase in mean bead brightness was measured and was attributed to Substrate cleavage by papain. The new type fluorescent amino acids seem to be a promising tool for the synthesis of fluorescent peptide ligands and fluorogenic protease substrates. (c) 2005 Elsevier Ltd. All rights reserved.