(S)-2-{(S)-4-methyl-2-[(S)-2-(2-oxoacetylamino)-3-phenylpropionylamino]pentanoylamino}pentanedioic acid dimethyl ester | 1235998-21-6

• 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-{(S)-4-methyl-2-[(S)-2-(2-oxoacetylamino)-3-phenylpropionylamino]pentanoylamino}pentanedioic acid dimethyl ester
• 英文别名: dimethyl (2S)-2-[[(2S)-4-methyl-2-[[(2S)-2-(oxaldehydoylamino)-3-phenylpropanoyl]amino]pentanoyl]amino]pentanedioate
• CAS: 1235998-21-6
• 化学式: C₂₄H₃₃N₃O₈
• 分子量: 491.541
• InChiKey: VFOSSPOXLARMTA-FHWLQOOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-甲氧基-1-(三甲基甲硅氧基)-2-甲基-1-丙烯 、 (S)-2-{(S)-4-methyl-2-[(S)-2-(2-oxoacetylamino)-3-phenylpropionylamino]pentanoylamino}pentanedioic acid dimethyl ester 以 水 为溶剂， 反应 24.0h， 以71%的产率得到(S)-2-{(S)-2-[(S)-2-(2-hydroxy-3-methoxycarbonyl-3-methylbutyrylamino)-3-phenylpropionylamino]-4-methylpentanoylamino}pentanedioic acid dimethyl 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：

  (S)-2-{(S)-2-[(S)-2-((S)-2-amino-3-hydroxypropionylamino)-3-phenylpropionylamino]-4-methylpentanoylamino}pentanedioic acid dimethyl ester 在 sodium periodate 作用下， 以 水 为溶剂， 以100%的产率得到(S)-2-{(S)-4-methyl-2-[(S)-2-(2-oxoacetylamino)-3-phenylpropionylamino]pentanoylamino}pentanedioic acid dimethyl 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。