2-[2-[2-[[(2S,3R)-2-[[(2S,3S,4R,5R)-4-[[(2S)-2-[[6-amino-2-[(1S)-3-amino-1-[[(2S)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxy-2,5-dimethylheptanoyl]amino]-3-hydroxybutanoyl]amino]ethyl]-1,3-thiazol-4-yl]-N-[3-[4-(3-aminopropylamino)butylamino]propyl]-1,3-thiazole-4-carboxamide | 1315270-96-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 2-[2-[2-[[(2S,3R)-2-[[(2S,3S,4R,5R)-4-[[(2S)-2-[[6-amino-2-[(1S)-3-amino-1-[[(2S)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxy-2,5-dimethylheptanoyl]amino]-3-hydroxybutanoyl]amino]ethyl]-1,3-thiazol-4-yl]-N-[3-[4-(3-aminopropylamino)butylamino]propyl]-1,3-thiazole-4-carboxamide
• CAS: 1315270-96-2
• 化学式: C₅₀H₈₁N₁₉O₉S₂
• 分子量: 1156.45
• InChiKey: AFEATFAHCYFJBC-GNCVJPDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  80
• 可旋转键数：
  38
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  523
• 氢给体数：
  16
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  、 (2S,3S,4R,5R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2,5-dimethyl-heptanoic acid 、 Fmoc-Thr-OH 、 pyrimidoblamic acid 、 Fmoc-DL-His(Trt)-OH 、 di-tert-butyl butane-1,4-diylbis((3-aminopropyl)carbamate) 、 2'-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-[2,4'-bithiazole]-4-carboxylic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium 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 0.75h， 生成 2-[2-[2-[[(2S,3R)-2-[[(2S,3S,4R,5R)-4-[[(2S)-2-[[6-amino-2-[(1S)-3-amino-1-[[(2S)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxy-2,5-dimethylheptanoyl]amino]-3-hydroxybutanoyl]amino]ethyl]-1,3-thiazol-4-yl]-N-[3-[4-(3-aminopropylamino)butylamino]propyl]-1,3-thiazole-4-carboxamide
  参考文献：
  名称：

  Deglycobleomycin A6 analogues modified in the methylvalerate moiety

  摘要：

  Previous studies have indicated that the methylvalerate subunit of bleomycin (BLM) plays an important role in facilitating DNA cleavage by BLM and deglycoBLM. Eleven methylvalerate analogues have been synthesized and incorporated into deglycoBLM congeners by the use of solid-phase synthesis. The effect of the valerate moiety in the deglycoBLM analogues has been studied by comparison with the parent deglycoBLM A(5) using supercoiled DNA relaxation and sequence-selective DNA cleavage assays. All of the deglycoBLM analogues were found to effect the relaxation of the plasmid DNA. Those analogues having aromatic C4-substituents exhibited cleavage efficiency comparable to that of deglycoBLM A(5). Some, but not all, of the deglycoBLM analogues were also capable of mediating sequence-selective DNA cleavage. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2011.04.047

文献信息

• Deglycobleomycin A6 analogues modified in the methylvalerate moiety
  作者：Xiaoqing Cai、Paul A. Zaleski、Ali Cagir、Sidney M. Hecht

  DOI：10.1016/j.bmc.2011.04.047

  日期：2011.6

  Previous studies have indicated that the methylvalerate subunit of bleomycin (BLM) plays an important role in facilitating DNA cleavage by BLM and deglycoBLM. Eleven methylvalerate analogues have been synthesized and incorporated into deglycoBLM congeners by the use of solid-phase synthesis. The effect of the valerate moiety in the deglycoBLM analogues has been studied by comparison with the parent deglycoBLM A(5) using supercoiled DNA relaxation and sequence-selective DNA cleavage assays. All of the deglycoBLM analogues were found to effect the relaxation of the plasmid DNA. Those analogues having aromatic C4-substituents exhibited cleavage efficiency comparable to that of deglycoBLM A(5). Some, but not all, of the deglycoBLM analogues were also capable of mediating sequence-selective DNA cleavage. (C) 2011 Published by Elsevier Ltd.