[3-({2'-[2-(2-{(2S,3S,4R)-4-[(2S,3R)-2-Amino-3-hydroxy-3-(1H-imidazol-4-yl)-propionylamino]-3-hydroxy-2-methyl-pentanoylamino}-acetylamino)-ethyl]-[2,4']bithiazolyl-4-carbonyl}-amino)-propyl]-dimethyl-sulfonium | 214619-11-1

• 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: [3-({2'-[2-(2-{(2S,3S,4R)-4-[(2S,3R)-2-Amino-3-hydroxy-3-(1H-imidazol-4-yl)-propionylamino]-3-hydroxy-2-methyl-pentanoylamino}-acetylamino)-ethyl]-[2,4']bithiazolyl-4-carbonyl}-amino)-propyl]-dimethyl-sulfonium
• CAS: 214619-11-1
• 化学式: C₂₈H₄₂N₉O₆S₃
• 分子量: 696.896
• InChiKey: DXQZWVYYDGSHEV-VTGWGJPASA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -0.67
• 重原子数：
  46.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  237.34
• 氢给体数：
  8.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  [3-({2'-[2-(2-{(2S,3S,4R)-4-[(2S,3R)-2-Amino-3-hydroxy-3-(1H-imidazol-4-yl)-propionylamino]-3-hydroxy-2-methyl-pentanoylamino}-acetylamino)-ethyl]-[2,4']bithiazolyl-4-carbonyl}-amino)-propyl]-dimethyl-sulfonium 在 二苯基膦叠氮化物 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 N^β-[1-amino-3(S)-[4-amino-6-[[[1(S)-[({4(S)-[({1(S)-[({2-[4'-({[(3-dimethylsulfonio)-1-propyl]amino}carbonyl)-2',4-bithiazol-2-yl]-1-ethyl}amino)carbonyl]methyl}amino)carbonyl]-3(S)-hydroxy-2(R)-pentyl}amino)carbonyl]-2(R)-hydroxy-2-.................
  参考文献：
  名称：

  A Systematic Evaluation of the Bleomycin A₂ l-Threonine Side Chain:  Its Role in Preorganization of a Compact Conformation Implicated in Sequence-Selective DNA Cleavage

  摘要：

  The preparation and examination of 3-7 are detailed and constitute analogues of deglycobleomycin A(2) (2) containing systematic modifications in the L-threonine side chain. The studies revealed a substantial impact of the substituent on the DNA cleavage efficiency and ratio of double strand/single strand (ds/ss) cleavage without affecting the characteristic 5'-GPy selectivity. The results of the comparisons proved consistent with conformational effects of the substituent within the linker domain which restrict the number of accessible conformations (Phi congruent to -120 degrees, Psi = 60-180 degrees) and favor adoption of a compact conformation (Phi congruent to -120 degrees, Psi congruent to 180 degrees) implicated in sequence-selective DNA cleavage. The studies also identify one potential site that may adopt two nearly equivalent turn conformations. This site may constitute one swivel point in the structure that permits access to a class of related bound structures (Psi = 60-180 degrees) adaptable to variable conformational characteristics required of multiple cleavage sites, including access to both strands of duplex DNA from a single intercalation site important for both primary and secondary DNA cleavage.

  DOI：

  10.1021/ja9816638
• 作为产物：
  描述：

  (2S,3R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(1-tritylimidazol-4-yl)propanoic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 [3-({2'-[2-(2-{(2S,3S,4R)-4-[(2S,3R)-2-Amino-3-hydroxy-3-(1H-imidazol-4-yl)-propionylamino]-3-hydroxy-2-methyl-pentanoylamino}-acetylamino)-ethyl]-[2,4']bithiazolyl-4-carbonyl}-amino)-propyl]-dimethyl-sulfonium
  参考文献：
  名称：

  A Systematic Evaluation of the Bleomycin A₂ l-Threonine Side Chain:  Its Role in Preorganization of a Compact Conformation Implicated in Sequence-Selective DNA Cleavage

  摘要：

  The preparation and examination of 3-7 are detailed and constitute analogues of deglycobleomycin A(2) (2) containing systematic modifications in the L-threonine side chain. The studies revealed a substantial impact of the substituent on the DNA cleavage efficiency and ratio of double strand/single strand (ds/ss) cleavage without affecting the characteristic 5'-GPy selectivity. The results of the comparisons proved consistent with conformational effects of the substituent within the linker domain which restrict the number of accessible conformations (Phi congruent to -120 degrees, Psi = 60-180 degrees) and favor adoption of a compact conformation (Phi congruent to -120 degrees, Psi congruent to 180 degrees) implicated in sequence-selective DNA cleavage. The studies also identify one potential site that may adopt two nearly equivalent turn conformations. This site may constitute one swivel point in the structure that permits access to a class of related bound structures (Psi = 60-180 degrees) adaptable to variable conformational characteristics required of multiple cleavage sites, including access to both strands of duplex DNA from a single intercalation site important for both primary and secondary DNA cleavage.

  DOI：

  10.1021/ja9816638