(S)-2-(2-oxoacetylamino)-propionic acid methyl ester | 1235998-19-2

• 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-(2-oxoacetylamino)-propionic acid methyl ester
• 英文别名: methyl (2S)-2-(oxaldehydoylamino)propanoate
• CAS: 1235998-19-2
• 化学式: C₆H₉NO₄
• 分子量: 159.142
• InChiKey: ZHNQSYOSQKXGSA-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-oxoacetylamino)-propionic acid methyl ester 、 1-ethylthio-1-(trimethylsiloxy)ethene 以 水 为溶剂， 反应 24.0h， 以12%的产率得到(S)-2-(3-ethylsulfanylcarbonyl-2-hydroxypropionylamino)propionic acid methyl ester
  参考文献：
  名称：

  Functionalization of Peptides and Proteins by Mukaiyama Aldol Reaction

  摘要：

  The scope of the catalyst-free water-based Mukaiyama aldol reaction was explored through its application to the site-selective functionalization of N-terminal aldehydes of peptides and proteins. Various functional groups were introduced under mild and environmentally friendly conditions, with the first demonstration of aldol C-C bond formation in protein labeling studies. The efficiency and speed achieved in protein labeling can be of special interest in chemical biology studies.

  DOI：

  10.1021/ja102733a
• 作为产物：
  描述：

  H-Ser-Ala-OMe 在 sodium periodate 作用下， 以 水 为溶剂， 以100%的产率得到(S)-2-(2-oxoacetylamino)-propionic acid methyl ester
  参考文献：
  名称：

  Functionalization of Peptides and Proteins by Mukaiyama Aldol Reaction

  摘要：

  The scope of the catalyst-free water-based Mukaiyama aldol reaction was explored through its application to the site-selective functionalization of N-terminal aldehydes of peptides and proteins. Various functional groups were introduced under mild and environmentally friendly conditions, with the first demonstration of aldol C-C bond formation in protein labeling studies. The efficiency and speed achieved in protein labeling can be of special interest in chemical biology studies.

  DOI：

  10.1021/ja102733a

文献信息

• Indium mediated allylation in peptide and protein functionalization
  作者：Jenefer Alam、Thomas H. Keller、Teck-Peng Loh

  DOI：10.1039/c1cc12926k

  日期：——

  Indium-mediated allylation has been used in the site-selective functionalization of N-terminal aldehydes of peptides and proteins. This is the first demonstration of indium-mediated C–C bond formation in protein labelling studies under mild and environmentally friendly conditions.

  铟介导的烯丙基化反应已被用于肽和蛋白质N端醛基的位点选择性功能化。这是在温和且环境友好的条件下，首次展示铟介导的C-C键形成在蛋白质标记研究中的应用。
• Functionalization of Peptides and Proteins by Mukaiyama Aldol Reaction
  作者：Jenefer Alam、Thomas H. Keller、Teck-Peng Loh

  DOI：10.1021/ja102733a

  日期：2010.7.21

  The scope of the catalyst-free water-based Mukaiyama aldol reaction was explored through its application to the site-selective functionalization of N-terminal aldehydes of peptides and proteins. Various functional groups were introduced under mild and environmentally friendly conditions, with the first demonstration of aldol C-C bond formation in protein labeling studies. The efficiency and speed achieved in protein labeling can be of special interest in chemical biology studies.