ethyl 3-[2-[[(2S)-4-amino-2-[[2-[[2-[[2-[2-[[[(2S)-4-amino-2-[[(2S)-3-hydroxy-2-[[2-[[[2-[[2-[[[2-[(2,2,2-trifluoroacetyl)amino]acetyl]amino]methyl]-1,3-thiazole-4-carbonyl]amino]acetyl]amino]methyl]-1,3-thiazole-4-carbonyl]amino]propanoyl]amino]-4-oxobutanoyl]amino]methyl]-1,3-thiazol-4-yl]-1,3-oxazole-4-carbonyl]amino]acetyl]amino]acetyl]amino]-4-oxobutanoyl]amino]acetyl]sulfanylpropanoate | 1265157-70-7

• 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: ethyl 3-[2-[[(2S)-4-amino-2-[[2-[[2-[[2-[2-[[[(2S)-4-amino-2-[[(2S)-3-hydroxy-2-[[2-[[[2-[[2-[[[2-[(2,2,2-trifluoroacetyl)amino]acetyl]amino]methyl]-1,3-thiazole-4-carbonyl]amino]acetyl]amino]methyl]-1,3-thiazole-4-carbonyl]amino]propanoyl]amino]-4-oxobutanoyl]amino]methyl]-1,3-thiazol-4-yl]-1,3-oxazole-4-carbonyl]amino]acetyl]amino]acetyl]amino]-4-oxobutanoyl]amino]acetyl]sulfanylpropanoate
• CAS: 1265157-70-7
• 化学式: C₄₆H₅₄F₃N₁₇O₁₈S₄
• 分子量: 1318.3
• InChiKey: NBIAZSGPEPYPPA-FKBYEOEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.5
• 重原子数：
  88
• 可旋转键数：
  37
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  645
• 氢给体数：
  14
• 氢受体数：
  29

反应信息

• 作为产物：
  描述：

  L-三氟乙酰甘氨酸 、 ethyl 3-(2-aminoacetylthio)propanoate hydrochloride 、 Fmoc-甘氨酸 、 FMOC-O-叔丁基-L-丝氨酸 、 Fmoc-N-三苯甲基-L-天冬酰胺 、 (S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid 、 2-[[[(9H-fluoren-9-yl)methoxy]carbonylamino]methyl]thiazole-4-carboxylic acid 、 Fmoc-Gly-Cys(Thz)-Ser(Oxz)-OH 在 N-甲基吗啉 、 [2-(5-chloro-2-triisopropylsilanylsulfanyl-phenyl)-ethyl]-methyl-carbamic acid tert-butyl ester 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 ethyl 3-[2-[[(2S)-4-amino-2-[[2-[[2-[[2-[2-[[[(2S)-4-amino-2-[[(2S)-3-hydroxy-2-[[2-[[[2-[[2-[[[2-[(2,2,2-trifluoroacetyl)amino]acetyl]amino]methyl]-1,3-thiazole-4-carbonyl]amino]acetyl]amino]methyl]-1,3-thiazole-4-carbonyl]amino]propanoyl]amino]-4-oxobutanoyl]amino]methyl]-1,3-thiazol-4-yl]-1,3-oxazole-4-carbonyl]amino]acetyl]amino]acetyl]amino]-4-oxobutanoyl]amino]acetyl]sulfanylpropanoate
  参考文献：
  名称：

  Total Synthesis of Microcin B17 via a Fragment Condensation Approach

  摘要：

  The total synthesis of the 43 amino acid antibacterial peptide Microcin B17 (MccB17) is described. The natural product was synthesized via a convergent approach from a heterocycle-derived peptide and peptide thioester fragments prepared via Fmoc-strategy solid phase peptide synthesis (SPPS). Final assembly was achieved in an efficient manner using two Ag(I)-assisted peptide ligation reactions to afford MccB17 in excellent overall yield.

  DOI：

  10.1021/ol102916b

文献信息

• Total Synthesis of Microcin B17 <i>via</i> a Fragment Condensation Approach
  作者：Robert E. Thompson、Katrina A. Jolliffe、Richard J. Payne

  DOI：10.1021/ol102916b

  日期：2011.2.18

  The total synthesis of the 43 amino acid antibacterial peptide Microcin B17 (MccB17) is described. The natural product was synthesized via a convergent approach from a heterocycle-derived peptide and peptide thioester fragments prepared via Fmoc-strategy solid phase peptide synthesis (SPPS). Final assembly was achieved in an efficient manner using two Ag(I)-assisted peptide ligation reactions to afford MccB17 in excellent overall yield.