(3-{2-[5-(3-aminopropylcarbamoyl)-1-methyl-1H-pyrrol-3-yl-carbamoyl]-4-nitropyrrol-1-yl}-propyl)-carbamic acid tert-butyl ester | 159539-43-2

• 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-[5-(3-aminopropylcarbamoyl)-1-methyl-1H-pyrrol-3-yl-carbamoyl]-4-nitropyrrol-1-yl}-propyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[3-[2-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-4-nitropyrrol-1-yl]propyl]carbamate
• CAS: 159539-43-2
• 化学式: C₂₄H₃₇N₇O₆
• 分子量: 519.601
• InChiKey: OGOFLDLUEIEFEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  155
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3-{2-[5-(3-aminopropylcarbamoyl)-1-methyl-1H-pyrrol-3-yl-carbamoyl]-4-nitropyrrol-1-yl}-propyl)-carbamic acid tert-butyl ester 在 三乙基硅烷 、 4-二甲氨基吡啶 、 氰基磷酸二乙酯 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.33h， 生成 N-[3-(dimethylamine)propyl]-1-methyl-4-[(1-{3-(2-amino-3-mercaptopropanamido)propyl}-4-{1-methyl-1H-imidazole-2-carboxamido}-1H-2-pyrrolyl)carboxamido]-1H-2-pyrrolecarboxamide
  参考文献：
  名称：

  Toward encoding reactivity using double-stranded DNA. Sequence-dependent native chemical ligation of DNA binding polyamides

  摘要：

  The coupling reaction between distamycin-related polyamides equipped with cysteine and thioester groups can be accelerated in the presence of double-stranded (ds) oligonucleotides with selected sequences. While the coupling reaction of reactive partners containing three pyrrole units is accelerated by dsDNAs containing ATTTTA or ATGTTA sites, the heterodimeric coupling between a tripyrrole and a polyamide equipped with two pyrroles and one imidazole, is accelerated by the latter DNA, but not by the other containing the A/T rich tract. These differences can be exploited for selecting preferred coupling pairs from a mixture of reactive monomers; therefore the reaction outcome depends on the instructions provided by the dsDNA sequence. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.126
• 作为产物：
  描述：

  4-硝基吡咯-2-羧酸乙酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 potassium carbonate 、 氯磷酸二乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 19.5h， 生成 (3-{2-[5-(3-aminopropylcarbamoyl)-1-methyl-1H-pyrrol-3-yl-carbamoyl]-4-nitropyrrol-1-yl}-propyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  通过合成的三吡咯-肽共轭物具有高亲和力，序列特异性的DNA结合。

  摘要：

  通过含氮系链将bZIP转录因子的基本区域连接至双霉素样三吡咯肽，可产生能够高亲和力识别特定的指定DNA序列的杂合体。氮在系链中的重要性由其被醚键取代引起的亲和力显着降低（超过10倍）表明。氨基丙基链在邻近带有含氮系链的吡咯的吡咯上的连接将亲和力增加约一个数量级。这些结果证实，质子化的胺基在设计的DNA结合肽上的合适位置提供了更高的亲和力，这很可能是由于与磷酸二酯主链形成了盐桥联的接触。

  DOI：

  10.1002/chem.200500010

文献信息

• Design, synthesis, and intracellular localization of a fluorescently labeled DNA binding polyamide related to the antibiotic distamycin
  作者：Sanjay K. Sharma、Andrew T. Morrissey、Gerald G. Miller、William H. Gmeiner、J.William Lown

  DOI：10.1016/s0960-894x(01)00064-6

  日期：2001.3

  The design and synthesis of the lipophilic (9) and fluorescent (10) conjugates of a structural analogue of distamycin and their in vitro cellular localization studies are reported. Confocal laser scanning microscopy (CLSM) indicates that 10 rapidly enters human ovarian adenocarcinoma (SKOV-3) cells with principal uptake in mitochondria and uniform cytoplasmic distribution.

  报道了双霉素结构类似物的亲脂性（9）和荧光（10）缀合物的设计和合成及其体外细胞定位研究。共聚焦激光扫描显微镜（CLSM）表明，有10个细胞迅速进入人卵巢腺癌细胞（SKOV-3），主要吸收线粒体并具有均匀的细胞质分布。
• High Affinity, Sequence Specific DNA Binding by Synthetic Tripyrrole-Peptide Conjugates
  作者：Juan B. Blanco、Olalla Vázquez、José Martínez-Costas、Luis Castedo、José L. Mascareñas

  DOI：10.1002/chem.200500010

  日期：2005.7.4

  basic region of a bZIP transcription factor to a distamycin-like tripyrrole peptide by means of a nitrogen-containing tether produces a hybrid capable of high-affinity recognition of specific, designated DNA sequences. The importance of the nitrogen in the tether is shown by the considerable reduction in affinity (more than 10-fold) caused by its replacement with an ether linkage. Attachment of an

  通过含氮系链将bZIP转录因子的基本区域连接至双霉素样三吡咯肽，可产生能够高亲和力识别特定的指定DNA序列的杂合体。氮在系链中的重要性由其被醚键取代引起的亲和力显着降低（超过10倍）表明。氨基丙基链在邻近带有含氮系链的吡咯的吡咯上的连接将亲和力增加约一个数量级。这些结果证实，质子化的胺基在设计的DNA结合肽上的合适位置提供了更高的亲和力，这很可能是由于与磷酸二酯主链形成了盐桥联的接触。
• Toward encoding reactivity using double-stranded DNA. Sequence-dependent native chemical ligation of DNA binding polyamides
  作者：Adrian Jiménez-Balsa、Verónica I. Dodero、José L. Mascareñas

  DOI：10.1016/j.tet.2013.05.126

  日期：2013.9

  The coupling reaction between distamycin-related polyamides equipped with cysteine and thioester groups can be accelerated in the presence of double-stranded (ds) oligonucleotides with selected sequences. While the coupling reaction of reactive partners containing three pyrrole units is accelerated by dsDNAs containing ATTTTA or ATGTTA sites, the heterodimeric coupling between a tripyrrole and a polyamide equipped with two pyrroles and one imidazole, is accelerated by the latter DNA, but not by the other containing the A/T rich tract. These differences can be exploited for selecting preferred coupling pairs from a mixture of reactive monomers; therefore the reaction outcome depends on the instructions provided by the dsDNA sequence. (C) 2013 Elsevier Ltd. All rights reserved.