O-1-(2-nitrophenyl)ethyl-O'-tert-butyl-N,N-diethyl phosphoramidite | 845619-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-1-(2-nitrophenyl)ethyl-O'-tert-butyl-N,N-diethyl phosphoramidite
• CAS: 845619-02-5
• 化学式: C₁₆H₂₇N₂O₄P
• 分子量: 342.375
• InChiKey: TVXYKCHDYCSMQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  64.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Nα-4-pentenoyl-L-serine cyanomethyl ester 、 O-1-(2-nitrophenyl)ethyl-O'-tert-butyl-N,N-diethyl phosphoramidite 在 4,5-二氰基咪唑 、 叔丁基过氧化氢 作用下， 以 四氢呋喃 、 癸烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以68.2%的产率得到Nα-4-pentenoyl-phospho(1-(2-nitrophenyl)ethyl-2-tert-butyl)-L-serine cyanomethyl ester
  参考文献：
  名称：

  Caged Phosphoproteins

  摘要：

  We present the chemical and biological synthesis of caged phosphoproteins using the in vitro nonsense codon suppression methodology. Specifically, phosphoamino acid analogues of serine, threonine, and tyrosine with a single photocleavable o-nitrophenylethyl caging group were synthesized as the amino acyl tRNA adducts for insertion into full-length proteins. For this purpose, a novel phosphitylating agent was developed. The successful incorporation of these bulky and charged amino acids into the alpha-subunit of the nicotinic acetyl choline receptor (nAChR) and the vasodilator-stimulated phosphoprotein (VASP) using an in vitro translation system is reported.

  DOI：

  10.1021/ja043875c
• 作为产物：
  描述：

  1-(2-硝基苯基)乙醇 、 六乙基亚磷酸胺 、 叔丁醇 在 4,5-二氰基咪唑 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到O-1-(2-nitrophenyl)ethyl-O'-tert-butyl-N,N-diethyl phosphoramidite
  参考文献：
  名称：

  Caged Phosphoproteins

  摘要：

  We present the chemical and biological synthesis of caged phosphoproteins using the in vitro nonsense codon suppression methodology. Specifically, phosphoamino acid analogues of serine, threonine, and tyrosine with a single photocleavable o-nitrophenylethyl caging group were synthesized as the amino acyl tRNA adducts for insertion into full-length proteins. For this purpose, a novel phosphitylating agent was developed. The successful incorporation of these bulky and charged amino acids into the alpha-subunit of the nicotinic acetyl choline receptor (nAChR) and the vasodilator-stimulated phosphoprotein (VASP) using an in vitro translation system is reported.

  DOI：

  10.1021/ja043875c