N,N'-(6-((6-hydroxyhexyl)carbamoyl)-2',7'-dimethyl-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl)-bis(N-ethyl-2,2,2-trifluoroacetamide) | 1355330-46-9

• 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: N,N'-(6-((6-hydroxyhexyl)carbamoyl)-2',7'-dimethyl-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl)-bis(N-ethyl-2,2,2-trifluoroacetamide)
• 英文别名: 6-(3',6'-N-ditrifluoroacetylrhodamine 6G-6-carboxamido)hexan-1-ol；3',6'-bis[ethyl-(2,2,2-trifluoroacetyl)amino]-N-(6-hydroxyhexyl)-2',7'-dimethyl-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-carboxamide
• CAS: 1355330-46-9
• 化学式: C₃₇H₃₇F₆N₃O₇
• 分子量: 749.707
• InChiKey: NIWKJHBONQHMBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  53
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  N,N'-(6-((6-hydroxyhexyl)carbamoyl)-2',7'-dimethyl-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl)-bis(N-ethyl-2,2,2-trifluoroacetamide) 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到(6-(3',6'-N-ditrifluoroacetylrhodamine 6G-6-carboxamido)hexyl)-1-O-(2-cyanoethyl)(N,N-diisopropyl)phosphoramidite
  参考文献：
  名称：

  Solid- and solution-phase synthesis and application of R6G dual-labeled oligonucleotide probes

  摘要：

  A novel N-TFA-protected carboxyrhodamine 6G (R6G) phosphoramidite was synthesized for use in an automated DNA synthesis to prepare 5'-labeled oligonucleotides. Deprotection and purification conditions were optimized for 5'-labeled and dual-labeled oligonucleotide probes. As an alternative we synthesized an azide derivative of R6G for CuAAC post-synthetic oligonucleotide labeling. Dual-labeled probes obtained by both methods showed the same efficacy in a quantitative PCR assay. R6G-labeled probes demonstrated superior properties in a qPCR assay in comparison with alternative HEX, JOE and SIMA dyes due to more efficient fluorescence quenching by BHQ-1. We successfully used R6G dual-labeled probes for rotavirus genotyping. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.041
• 作为产物：
  描述：

  3-(乙基氨基)-4-甲酚 在 N-羟基丁二酰亚胺 、 甲烷磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N,N'-(6-((6-hydroxyhexyl)carbamoyl)-2',7'-dimethyl-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl)-bis(N-ethyl-2,2,2-trifluoroacetamide)
  参考文献：
  名称：

  Solid- and solution-phase synthesis and application of R6G dual-labeled oligonucleotide probes

  摘要：

  A novel N-TFA-protected carboxyrhodamine 6G (R6G) phosphoramidite was synthesized for use in an automated DNA synthesis to prepare 5'-labeled oligonucleotides. Deprotection and purification conditions were optimized for 5'-labeled and dual-labeled oligonucleotide probes. As an alternative we synthesized an azide derivative of R6G for CuAAC post-synthetic oligonucleotide labeling. Dual-labeled probes obtained by both methods showed the same efficacy in a quantitative PCR assay. R6G-labeled probes demonstrated superior properties in a qPCR assay in comparison with alternative HEX, JOE and SIMA dyes due to more efficient fluorescence quenching by BHQ-1. We successfully used R6G dual-labeled probes for rotavirus genotyping. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.041

文献信息

• Rhodamine lactone phosphoramidites and polymers
  申请人：Diwu Zhenjun

  公开号：US20120016128A1

  公开（公告）日：2012-01-19

  The present invention provides rhodamine lactone phosphoramidites and polymer compositions, methods for making these phosphoramidites and polymer compositions, and methods for using these phosphoramidites and polymer compositions for labeling oligonucleotides. In particular, the present invention provides compositions and methods for labeling the 3′- and 5′-end of oligonucleotides during synthesis of the oligonucleotides.

  本发明提供了罗丹明内酯磷酰胺酯和聚合物组成物、制备这些磷酰胺酯和聚合物组成物的方法以及使用这些磷酰胺酯和聚合物组成物标记寡核苷酸的方法。特别地，本发明提供了在合成寡核苷酸过程中标记寡核苷酸的3'-和5'-末端的组成物和方法。
• Solid- and solution-phase synthesis and application of R6G dual-labeled oligonucleotide probes
  作者：Aleksander Yu. Skoblov、Maxim V. Vichuzhanin、Valentina M. Farzan、Olga A. Veselova、Tatiana A. Konovalova、Alexander T. Podkolzin、German A. Shipulin、Timofei S. Zatsepin

  DOI：10.1016/j.bmc.2015.08.041

  日期：2015.10

  A novel N-TFA-protected carboxyrhodamine 6G (R6G) phosphoramidite was synthesized for use in an automated DNA synthesis to prepare 5'-labeled oligonucleotides. Deprotection and purification conditions were optimized for 5'-labeled and dual-labeled oligonucleotide probes. As an alternative we synthesized an azide derivative of R6G for CuAAC post-synthetic oligonucleotide labeling. Dual-labeled probes obtained by both methods showed the same efficacy in a quantitative PCR assay. R6G-labeled probes demonstrated superior properties in a qPCR assay in comparison with alternative HEX, JOE and SIMA dyes due to more efficient fluorescence quenching by BHQ-1. We successfully used R6G dual-labeled probes for rotavirus genotyping. (c) 2015 Elsevier Ltd. All rights reserved.