[3-({2'-[2-((2S,3R)-2-{(R)-4-[(2S,3R)-2-Amino-3-hydroxy-3-(1H-imidazol-4-yl)-propionylamino]-pentanoylamino}-3-hydroxy-butyrylamino)-ethyl]-[2,4']bithiazolyl-4-carbonyl}-amino)-propyl]-dimethyl-sulfonium | 214402-55-8

• 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-((2S,3R)-2-{(R)-4-[(2S,3R)-2-Amino-3-hydroxy-3-(1H-imidazol-4-yl)-propionylamino]-pentanoylamino}-3-hydroxy-butyrylamino)-ethyl]-[2,4']bithiazolyl-4-carbonyl}-amino)-propyl]-dimethyl-sulfonium
• CAS: 214402-55-8
• 化学式: C₂₉H₄₄N₉O₆S₃
• 分子量: 710.923
• InChiKey: ZBUHDOCRODCZCA-TYOWYHOZSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -0.14
• 重原子数：
  47.0
• 可旋转键数：
  19.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 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-((2S,3R)-2-{(R)-4-[(2S,3R)-2-Amino-3-hydroxy-3-(1H-imidazol-4-yl)-propionylamino]-pentanoylamino}-3-hydroxy-butyrylamino)-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 12.5h， 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]-2(R)-hydroxy-1-propyl}amino)carbonyl]-2(R)-butyl}amino)carbonyl]-2(R)-hydroxy-2-(imidazol-4-yl)
  参考文献：
  名称：

  Definition of the Effect and Role of the Bleomycin A₂ Valerate Substituents:  Preorganization of a Rigid, Compact Conformation Implicated in Sequence-Selective DNA Cleavage

  摘要：

  The synthesis and a comparative study of deglycobleomycin A(2) analogues containing key modifications in the valerate subunit are described in efforts that define the role of the linker length and its substituents. In addition to demonstrating that the C3-hydroxy group exhibits only a modest effect (1-2x) that may be attributed to an intermolecular H-bond with DNA and that the length of the linker is important (C4 > C5 > C3 > C2), the studies illustrate that the substantial impact of the C4-methyl group is linked to the presence of the C2-methyl group, while the modest impact of the C2-methyl group itself (ca. 2x) is not coupled to the presence of the C4-methyl group. These effects may be explained by the conformational properties of the agents resulting from the substitutions and beautifully fit the models of DNA-bound Co(III)OOH bleomycin A(2) and deglycobleomycin A(2). The magnitude of the effects suggests that an important functional role of the linker region is to facilitate adoption of a rigid, compact conformation productive for DNA cleavage. The studies also identify a second potential site that may adopt two nearly equivalent conformations which may constitute a swivel point that permits access to a class of related bound structures adaptable to the conformational characteristics of the multiple cleavage sites or access to both strands of DNA from a common intercalation site important for both primary (single strand) and secondary (double strand) cleavage.

  DOI：

  10.1021/ja9816640
• 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 12.0h， 生成 [3-({2'-[2-((2S,3R)-2-{(R)-4-[(2S,3R)-2-Amino-3-hydroxy-3-(1H-imidazol-4-yl)-propionylamino]-pentanoylamino}-3-hydroxy-butyrylamino)-ethyl]-[2,4']bithiazolyl-4-carbonyl}-amino)-propyl]-dimethyl-sulfonium
  参考文献：
  名称：

  Definition of the Effect and Role of the Bleomycin A₂ Valerate Substituents:  Preorganization of a Rigid, Compact Conformation Implicated in Sequence-Selective DNA Cleavage

  摘要：

  The synthesis and a comparative study of deglycobleomycin A(2) analogues containing key modifications in the valerate subunit are described in efforts that define the role of the linker length and its substituents. In addition to demonstrating that the C3-hydroxy group exhibits only a modest effect (1-2x) that may be attributed to an intermolecular H-bond with DNA and that the length of the linker is important (C4 > C5 > C3 > C2), the studies illustrate that the substantial impact of the C4-methyl group is linked to the presence of the C2-methyl group, while the modest impact of the C2-methyl group itself (ca. 2x) is not coupled to the presence of the C4-methyl group. These effects may be explained by the conformational properties of the agents resulting from the substitutions and beautifully fit the models of DNA-bound Co(III)OOH bleomycin A(2) and deglycobleomycin A(2). The magnitude of the effects suggests that an important functional role of the linker region is to facilitate adoption of a rigid, compact conformation productive for DNA cleavage. The studies also identify a second potential site that may adopt two nearly equivalent conformations which may constitute a swivel point that permits access to a class of related bound structures adaptable to the conformational characteristics of the multiple cleavage sites or access to both strands of DNA from a common intercalation site important for both primary (single strand) and secondary (double strand) cleavage.

  DOI：

  10.1021/ja9816640