S-[2-(methylamino)-2-oxoethyl] (2S)-2-acetamido-3-phenylpropanethioate | 289038-92-2

• 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: S-[2-(methylamino)-2-oxoethyl] (2S)-2-acetamido-3-phenylpropanethioate
• CAS: 289038-92-2
• 化学式: C₁₄H₁₈N₂O₃S
• 分子量: 294.375
• InChiKey: ROXDXEDKIWJNCB-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-[2-(methylamino)-2-oxoethyl] (2S)-2-acetamido-3-phenylpropanethioate 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 28.0h， 生成 AcPheGlyNHBn
  参考文献：
  名称：

  Staudinger Ligation:  A Peptide from a Thioester and Azide

  摘要：

  The technique of native chemical ligation enables the total chemical synthesis of proteins. This method is limited, however, by an absolute requirement for a cysteine residue at the ligation juncture. Here, this restriction is overcome with a new chemical ligation method in which a phosphinobenzenethiol is used to link a thioester and azide. The product is an amide with no residual atoms.

  DOI：

  10.1021/ol0060174
• 作为产物：
  描述：

  n-甲基-硫代乙酰胺 、 N-乙酰-L-苯丙氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以92%的产率得到S-[2-(methylamino)-2-oxoethyl] (2S)-2-acetamido-3-phenylpropanethioate
  参考文献：
  名称：

  Staudinger Ligation:  A Peptide from a Thioester and Azide

  摘要：

  The technique of native chemical ligation enables the total chemical synthesis of proteins. This method is limited, however, by an absolute requirement for a cysteine residue at the ligation juncture. Here, this restriction is overcome with a new chemical ligation method in which a phosphinobenzenethiol is used to link a thioester and azide. The product is an amide with no residual atoms.

  DOI：

  10.1021/ol0060174

文献信息

• Staudinger Ligation:  A Peptide from a Thioester and Azide
  作者：Bradley L. Nilsson、Laura L. Kiessling、Ronald T. Raines

  DOI：10.1021/ol0060174

  日期：2000.6.1

  The technique of native chemical ligation enables the total chemical synthesis of proteins. This method is limited, however, by an absolute requirement for a cysteine residue at the ligation juncture. Here, this restriction is overcome with a new chemical ligation method in which a phosphinobenzenethiol is used to link a thioester and azide. The product is an amide with no residual atoms.