(S)-2-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-hydroxypropionylamino)-3-phenylpropionylamino]-4-methylpentanoic acid methyl ester | 1235998-13-6

• 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)-2-((S)-2-tert-butoxycarbonylamino-3-hydroxypropionylamino)-3-phenylpropionylamino]-4-methylpentanoic acid methyl ester
• CAS: 1235998-13-6
• 化学式: C₂₄H₃₇N₃O₇
• 分子量: 479.574
• InChiKey: IVJLXSOSZNRUGV-FHWLQOOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  143.06
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-hydroxypropionylamino)-3-phenylpropionylamino]-4-methylpentanoic acid methyl ester 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以100%的产率得到(S)-2-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-hydroxypropionylamino)-3-phenylpropionylamino]-4-methylpentanoic acid
  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：

  L-亮氨酸甲酯盐酸盐 、 N-tert-Butoxycarbonyl-L-seryl-L-phenylalanin 在 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(S)-2-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-hydroxypropionylamino)-3-phenylpropionylamino]-4-methylpentanoic 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