(S)-4-((2S,3R)-2-((S)-2-((S)-2-amino-4-methylpentanamido)-3-hydroxypropanamido)-3-hydroxybutanamido)-5-(((S)-3-hydroxy-1-((S)-2-(mercaptomethyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)amino)-5-oxopentanoic acid | 1445907-67-4

• 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)-4-((2S,3R)-2-((S)-2-((S)-2-amino-4-methylpentanamido)-3-hydroxypropanamido)-3-hydroxybutanamido)-5-(((S)-3-hydroxy-1-((S)-2-(mercaptomethyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)amino)-5-oxopentanoic acid
• CAS: 1445907-67-4
• 化学式: C₂₆H₄₆N₆O₁₀S
• 分子量: 634.751
• InChiKey: FNMKDXGKHLZAEY-IALLDWONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.55
• 重原子数：
  43.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  260.72
• 氢给体数：
  10.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (S)-6-amino-N-((S)-1-(((S)-1-(((S)-1-amino-1-oxopropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-1-oxopropan-2-yl)-2-((S)-2-((R)-2-amino-3-mercaptopropanamido)propanamido)hexanamide 、 (S)-4-((2S,3R)-2-((S)-2-((S)-2-amino-4-methylpentanamido)-3-hydroxypropanamido)-3-hydroxybutanamido)-5-(((S)-3-hydroxy-1-((S)-2-(mercaptomethyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)amino)-5-oxopentanoic acid 在 4-巯基苯基乙酸 、 sodium acetate 作用下， 以 aq. buffer 为溶剂， 反应 0.83h， 生成 H-LSTESCAKAFA-NH2
  参考文献：
  名称：

  Chemical synthesis of N-peptidyl 2-pyrrolidinemethanethiol for peptide ligation

  摘要：

  Peptides carrying a C-terminal 2-pyrrolidinemethanethiol (PMT) unit were synthesized using 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS), and were shown to ligate efficiently with cysteinyl-peptides. This novel PMT-mediated ligation tolerated many different C-terminal residues and was successfully applied to a one-pot N-to-C sequential ligation reaction and the semi-synthesis of lysine 16 acetylated histone H4, demonstrating the utility of the method in peptide and protein synthesis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.013
• 作为产物：
  描述：

  Fmoc-L-亮氨酸 、 、 FMOC-O-叔丁基-L-丝氨酸 、 Fmoc-O-叔丁基-L-谷氨酸 、 O-(叔丁基)-N-[9H-芴-9-甲氧羰基]-D-别苏氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.83h， 生成 (S)-4-((2S,3R)-2-((S)-2-((S)-2-amino-4-methylpentanamido)-3-hydroxypropanamido)-3-hydroxybutanamido)-5-(((S)-3-hydroxy-1-((S)-2-(mercaptomethyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)amino)-5-oxopentanoic acid
  参考文献：
  名称：

  Chemical synthesis of N-peptidyl 2-pyrrolidinemethanethiol for peptide ligation

  摘要：

  Peptides carrying a C-terminal 2-pyrrolidinemethanethiol (PMT) unit were synthesized using 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS), and were shown to ligate efficiently with cysteinyl-peptides. This novel PMT-mediated ligation tolerated many different C-terminal residues and was successfully applied to a one-pot N-to-C sequential ligation reaction and the semi-synthesis of lysine 16 acetylated histone H4, demonstrating the utility of the method in peptide and protein synthesis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.013