N-{3-[4-((S)-2-tert-Butoxycarbonylamino-2-carboxy-ethyl)-phenyl]-prop-2-ynyl}-6-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-isophthalamic acid | 383372-58-5

• 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-{3-[4-((S)-2-tert-Butoxycarbonylamino-2-carboxy-ethyl)-phenyl]-prop-2-ynyl}-6-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-isophthalamic acid
• 英文别名: 5-[3-[4-[(2S)-2-carboxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]phenyl]prop-2-ynylcarbamoyl]-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• CAS: 383372-58-5
• 化学式: C₃₈H₃₂N₂O₁₀
• 分子量: 676.679
• InChiKey: ZVRBLKRUFBWJLL-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  189
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-{3-[4-((S)-2-tert-Butoxycarbonylamino-2-carboxy-ethyl)-phenyl]-prop-2-ynyl}-6-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-isophthalamic acid 在 三氟乙酸 作用下， 以88%的产率得到N-{3-[4-((S)-2-Amino-2-carboxy-ethyl)-phenyl]-prop-2-ynyl}-6-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-isophthalamic acid
  参考文献：
  名称：

  FLUORESCENCE RESONANCE ENERGY TRANSFER DYE NUCLEOTIDE TERMINATORS: A NEW SYNTHETIC APPROACH FOR HIGH-THROUGHOUT DNA SEQUENCING

  摘要：

  Fluorescence resonance energy transfer (FRET) based dye-nucleotide terminators (10-13) were designed, synthesized, and formulated with Thermo Sequenase(TM) II DNA polymerase into a robust kit for high throughput DNA sequencing. The key energy transfer (ET) rigid and linear linker (2), required for the syntheses of energy transfer cassettes (6-9) was synthesized via Heck coupling reaction on t-Boc-L-4-iodo-phenylalanine (1) with N-TFA-propargylamine.

  DOI：

  10.1081/ncn-100002307
• 作为产物：
  描述：

  Boc-4-碘-L-苯丙氨酸 在 ammonium hydroxide 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-{3-[4-((S)-2-tert-Butoxycarbonylamino-2-carboxy-ethyl)-phenyl]-prop-2-ynyl}-6-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-isophthalamic acid
  参考文献：
  名称：

  FLUORESCENCE RESONANCE ENERGY TRANSFER DYE NUCLEOTIDE TERMINATORS: A NEW SYNTHETIC APPROACH FOR HIGH-THROUGHOUT DNA SEQUENCING

  摘要：

  Fluorescence resonance energy transfer (FRET) based dye-nucleotide terminators (10-13) were designed, synthesized, and formulated with Thermo Sequenase(TM) II DNA polymerase into a robust kit for high throughput DNA sequencing. The key energy transfer (ET) rigid and linear linker (2), required for the syntheses of energy transfer cassettes (6-9) was synthesized via Heck coupling reaction on t-Boc-L-4-iodo-phenylalanine (1) with N-TFA-propargylamine.

  DOI：

  10.1081/ncn-100002307