boc(tos)-his-tyr-ome | 1395056-07-1

• 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: boc(tos)-his-tyr-ome
• CAS: 1395056-07-1
• 化学式: C₂₈H₃₄N₄O₈S
• 分子量: 586.666
• InChiKey: IXHJNAQJNFCLKA-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  165.92
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,10-菲罗啉 、 boc(tos)-his-tyr-ome 在 copper(II) acetate monohydrate 、 sodium perchlorate monohydrate 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以85%的产率得到[Cu(II)(boc(tos)-his-tyr-ome)(phen)](ClO4)2
  参考文献：
  名称：

  Synthesis and characterization of novel square planar copper(II)–dipeptide–1,10-phenanthroline complexes: Investigation of their DNA binding and cleavage properties

  摘要：

  In view of the importance of aromatic moieties in DNA binding and cleavage, two new Cu(II)-dipeptide-phen (phen = 1,10-phenanthroline) complexes, viz. [Cu(II)(boc(tos)-his-trp-ome)(phen)](ClO4)(2) (1) and [Cu(II)(boc(tos)-his-tyr-ome)(phen)](ClO4)(2) (2) were synthesized, comprehensively characterized and their structures reported. The physico-chemical data and molecular modeling approaches support that the complexes are arranged in a distorted square planar geometry. To provide an insight on the mode and affinity of the interaction of these complexes with calf thymus (CT) DNA the following experiments were carried out: thermal denaturation (T-m), UV-Vis absorption, competitive binding, viscosity and fluorescence spectroscopy studies. These experimental results indicate that the complexes interact through stacking between the base pairs of double helix DNA. The overall binding constants (K-b) were determined as 3.33 x 10(4) and 2.82 x 10(4) M-1 for 1 and 2 respectively. The complexes converted supercoiled plasmid pUC19 DNA (SC DNA) into its nicked (NC) form both in the absence (hydrolytic cleavage) and presence (oxidative cleavage) of H2O2. The control experiments demonstrate that no diffusible radical species were involved in the hydrolytic cleavage, but in the presence of H2O2, hydroxyl radical (OH center dot) species were generated and initiated the cleavage reaction by an oxidative pathway. The rate constants for the hydrolysis of the phosphodiester bond were determined as 1.70 h(-1) and 1.82 h(-1) for 1 and 2 respectively. This amounts to a (4.7-5.0) x 10(7)-fold rate enhancement compared to non-catalyzed DNA cleavage, which is significant. These complexes exhibit better DNA binding and cleavage abilities compared to similar reported complexes. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.05.046
• 作为产物：
  描述：

  L-酪氨酸甲酯 、 N-叔丁氧羰基-N(咪唑)-(4-甲基苯磺酰基)-L-组氨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 boc(tos)-his-tyr-ome
  参考文献：
  名称：

  Synthesis and characterization of novel square planar copper(II)–dipeptide–1,10-phenanthroline complexes: Investigation of their DNA binding and cleavage properties

  摘要：

  In view of the importance of aromatic moieties in DNA binding and cleavage, two new Cu(II)-dipeptide-phen (phen = 1,10-phenanthroline) complexes, viz. [Cu(II)(boc(tos)-his-trp-ome)(phen)](ClO4)(2) (1) and [Cu(II)(boc(tos)-his-tyr-ome)(phen)](ClO4)(2) (2) were synthesized, comprehensively characterized and their structures reported. The physico-chemical data and molecular modeling approaches support that the complexes are arranged in a distorted square planar geometry. To provide an insight on the mode and affinity of the interaction of these complexes with calf thymus (CT) DNA the following experiments were carried out: thermal denaturation (T-m), UV-Vis absorption, competitive binding, viscosity and fluorescence spectroscopy studies. These experimental results indicate that the complexes interact through stacking between the base pairs of double helix DNA. The overall binding constants (K-b) were determined as 3.33 x 10(4) and 2.82 x 10(4) M-1 for 1 and 2 respectively. The complexes converted supercoiled plasmid pUC19 DNA (SC DNA) into its nicked (NC) form both in the absence (hydrolytic cleavage) and presence (oxidative cleavage) of H2O2. The control experiments demonstrate that no diffusible radical species were involved in the hydrolytic cleavage, but in the presence of H2O2, hydroxyl radical (OH center dot) species were generated and initiated the cleavage reaction by an oxidative pathway. The rate constants for the hydrolysis of the phosphodiester bond were determined as 1.70 h(-1) and 1.82 h(-1) for 1 and 2 respectively. This amounts to a (4.7-5.0) x 10(7)-fold rate enhancement compared to non-catalyzed DNA cleavage, which is significant. These complexes exhibit better DNA binding and cleavage abilities compared to similar reported complexes. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.05.046