Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-tetrahydro-pyran-3-yl ester | 861668-76-0

• 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: Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-tetrahydro-pyran-3-yl ester
• CAS: 861668-76-0
• 化学式: C₂₀H₂₅N₃O₁₂
• 分子量: 499.431
• InChiKey: VIZZCQFVUFTWNW-BFMVXSJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.25
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  191.6
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-tetrahydro-pyran-3-yl ester 在 palladium on activated charcoal 碳酸二异丙酯 、 氢气 、 1-羟基苯并三唑 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-({4-[4-({4-[(1H-indole-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carbonyl}-amino)-butyrylamino]-1-methyl-1H-pyrrole-2-carbonyl}-amino)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Carbohydrate-Based DNA Ligands:  Sugar−Oligoamides as a Tool to Study Carbohydrate−Nucleic Acid Interactions

  摘要：

  Sugar-oligoamides have been designed and synthesized as structurally simple carbohydrate-based ligands to study carbohydrate-DNA interactions. The general design of the ligands 1-3 has been done as to favor the bound conformation of Distamycin-type gamma-linked covalent dimers which is a hairpin conformation. Indeed, NMR analysis of the sugar-oligoamides in the free state has indicated the presence of a percentage of a hairpin conformation in aqueous solution. The DNA binding activity of compounds 1-3 was confirmed by calf thymus DNA (ct-DNA) NMR titration. Interestingly, the binding of the different sugar-oligoamides seems to be modulated by the sugar configuration. Semiquantitative structural information about the DNA ligand complexes has been derived from NMR data. A competition experiment with Netropsin suggested that the sugar-oligoamide 3 bind to DNA in the minor groove. The NMR titrations of 1-3 with poly(dA-dT) and poly(dG-dC) suggested preferential binding to the ATAT sequence. TR-NOE NMR experiments for the sugar-oligoamide 3-ct-DNA complex both in D2O and H2O have confirmed the complex formation and given information on the conformation of the ligand in the bound state. The data confirmed that the sugar-oligoamide ligand is a hairpin in the bound state. Even more relevant to our goal, structural information on the conformation around the N-glycosidic linkage has been accessed. Thus, the sugar asymmetric centers pointing to the NH-amide and N-methyl rims of the molecule have been characterized.

  DOI：

  10.1021/ja050794n
• 作为产物：
  描述：

  1-甲基-4-硝基吡咯-2-羧酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Carbohydrate-Based DNA Ligands:  Sugar−Oligoamides as a Tool to Study Carbohydrate−Nucleic Acid Interactions

  摘要：

  Sugar-oligoamides have been designed and synthesized as structurally simple carbohydrate-based ligands to study carbohydrate-DNA interactions. The general design of the ligands 1-3 has been done as to favor the bound conformation of Distamycin-type gamma-linked covalent dimers which is a hairpin conformation. Indeed, NMR analysis of the sugar-oligoamides in the free state has indicated the presence of a percentage of a hairpin conformation in aqueous solution. The DNA binding activity of compounds 1-3 was confirmed by calf thymus DNA (ct-DNA) NMR titration. Interestingly, the binding of the different sugar-oligoamides seems to be modulated by the sugar configuration. Semiquantitative structural information about the DNA ligand complexes has been derived from NMR data. A competition experiment with Netropsin suggested that the sugar-oligoamide 3 bind to DNA in the minor groove. The NMR titrations of 1-3 with poly(dA-dT) and poly(dG-dC) suggested preferential binding to the ATAT sequence. TR-NOE NMR experiments for the sugar-oligoamide 3-ct-DNA complex both in D2O and H2O have confirmed the complex formation and given information on the conformation of the ligand in the bound state. The data confirmed that the sugar-oligoamide ligand is a hairpin in the bound state. Even more relevant to our goal, structural information on the conformation around the N-glycosidic linkage has been accessed. Thus, the sugar asymmetric centers pointing to the NH-amide and N-methyl rims of the molecule have been characterized.

  DOI：

  10.1021/ja050794n

文献信息

• Sugar–Oligoamides: Bound-State Conformation and DNA Minor-Groove-Binding Description by TR-NOESY and Differential-Frequency Saturation-Transfer-Difference Experiments
  作者：Florence Souard、Eva Muñoz、Pablo Peñalver、Concepción Badía、Rafael del Villar-Guerra、Juan Luis Asensio、Jesús Jiménez-Barbero、Cristina Vicent

  DOI：10.1002/chem.200701103

  日期：2008.3.7

  Selective-frequency saturation-transfer-difference (STD) spectra allow the description of complexes established between minor-groove binders and long tracts of calf thymus DNA (ct-DNA). Two sets of experiments with selective saturation of either the H1' or H4'/H5'/H5'' proton NMR regions of deoxyribose allow the description of the ligand residues close to the inner (H1') and outer regions (H4'/H5'/H5'')

  选择性频率饱和转移差异（STD）光谱可以描述在小沟结合物和小牛胸腺DNA（ct-DNA）的长片段之间建立的复合物。通过对脱氧核糖的H1'或H4'/ H5'/ H5''质子NMR区域进行选择性饱和的两组实验，可以描述靠近内部区域（H1'）和外部区域（H4'/ H5）的配体残基'/ H5''）双螺旋DNA的小沟。TR-NOESY和STD实验都研究了一系列糖寡核苷酸（2-6）与ct-DNA的配合物。配合物的结合模式类似于netropsin（1），使我们能够为该配体家族定义一般的结合模式，其中NH边缘指向DNA的小沟的内部区域（内部区域），CH3边缘指向DNA的小沟的外部部分（外部区域）。同样通过TR-NOESY和STD实验，已经获得了糖残基的不对称中心靠近凹槽的内部和外部的描述。这些结果证实糖是造成先前在结合能学中发现的差异的原因。