4-(3-Amino-1-propyn-1-yl)-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine | 260397-84-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(3-Amino-1-propyn-1-yl)-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine
• 英文别名: (2S)-3-[4-(3-aminoprop-1-ynyl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 260397-84-0
• 化学式: C₁₇H₂₂N₂O₄
• 分子量: 318.373
• InChiKey: KDIBYIIEIANKAN-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3-Amino-1-propyn-1-yl)-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二甲基亚砜 为溶剂， 生成 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：

  (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[3-[(2,2,2-trifluoroacetyl)amino]prop-1-ynyl]phenyl]propanoic acid 在 ammonium hydroxide 作用下， 以100%的产率得到4-(3-Amino-1-propyn-1-yl)-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine
  参考文献：
  名称：

  Fluorescence resonance energy transfer terminators for DNA sequencing

  摘要：

  A four-colour set of fluorescence resonance energy transfer dideoxy nucleotide terminators (10-13), have been synthesised using a rigid and linear tri-functional molecule (2), synthesised via Heck coupling reaction of t-Boc-L-4-iodophenylalanine (1) with N-TFA-propargylamine. Evaluation of the terminators in DNA sequencing reactions, in combination with Thermo Sequenase(TM) II DNA polymerase, demonstrated them to be excellent reagents for high-throughput DNA sequencing. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01617-8