5-carboxyrhodamine 6G

• 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: 5-carboxyrhodamine 6G
• 英文别名: 4-[3-(Ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzene-1,3-dicarboxylic acid;hydrochloride；4-[3-(ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzene-1,3-dicarboxylic acid;hydrochloride
• 化学式: C₂₇H₂₆N₂O₅*ClH
• 分子量: 494.975
• InChiKey: VSYBZFNXXNHSAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-(乙基氨基)-4-甲酚 、 N,N-二甲基甲酰胺 、 偏苯三酸酐 在 甲烷磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 49.0h， 以26.1%的产率得到5-carboxyrhodamine 6G
  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

• 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.