diethyl 3,3'-bis(3-hydroxypropyl)-4,4'-dimethyl-2,2'-dipyrrylmethane-5,5-dicarboxylate | 202583-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: diethyl 3,3'-bis(3-hydroxypropyl)-4,4'-dimethyl-2,2'-dipyrrylmethane-5,5-dicarboxylate
• 英文别名: ethyl 5-[[5-ethoxycarbonyl-3-(3-hydroxypropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-4-(3-hydroxypropyl)-3-methyl-1H-pyrrole-2-carboxylate
• CAS: 202583-54-8
• 化学式: C₂₃H₃₄N₂O₆
• 分子量: 434.533
• InChiKey: WVPZYEHWGBIOSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 3,3'-bis(3-hydroxypropyl)-4,4'-dimethyl-2,2'-dipyrrylmethane-5,5-dicarboxylate 在 sodium hydroxide 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 35.0h， 生成 3-[2-[[3-(3-hydroxypropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-4-methyl-1H-pyrrol-3-yl]propan-1-ol
  参考文献：
  名称：

  A Porphyrin Embedded in DNA

  摘要：

  Oligodeoxynucleotides containing an alkylporphyrin linked to the phosphate groups of DNA via oxypropyl chains have been synthesized. To our knowledge, these are the first porphyrin-nucleic acid conjugates bearing the porphyrin embedded in the backbone of DNA. Chain assembly was achieved by automated solid-phase synthesis using a dimethoxytrityl-protected porphyrin phosphoramidite and standard DNA building blocks. The thermal stability of duplexes involving the octadecamer 5'-CGCGCCTTC-P-CATTGCGG-3', where -P- denotes the porphyrin, was found to depend on the sequence of the complementary strand., A duplex where a thymidine residue in the complementary strand faces the porphyrin gives a higher melting point than duplexes bearing an abasic site or a dT(3) loop at this position. Duplex formation is accompanied by 180% hypochromicity at 501 nm, and other spectral changes unprecedented in porphyrinoids interacting with nucleic acids. Footprinting with nuclease S1, together with CD spectropolarimetry, indicates that the alkylporphyrin is embedded in a B-type duplex, with highly nuclease-sensitive phosphates only in the local environment of the porphyrin. Peak shifts in the NMR spectrum of the porphyrin-containing duplex, together with. fluorescence data, point toward an interaction between the porphyrin and the stacked nucleobases. Porphyrin-containing DNA-and RNA-duplexes, conveniently prepared with the porphyrin phosphoramidite described here, are expected to be valuable for photochemical and electron-transfer studies, as well as potential cofactor-using nucleic acid-based enzymes which could have had a role in prebiotic evolution.

  DOI：

  10.1021/jo9718051
• 作为产物：
  描述：

  4,4'-bis-(2-methoxycarbonyl-ethyl)-3,3'-dimethyl-5,5'-methanediyl-bis-pyrrole-2-carboxylic acid diethyl ester 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到diethyl 3,3'-bis(3-hydroxypropyl)-4,4'-dimethyl-2,2'-dipyrrylmethane-5,5-dicarboxylate
  参考文献：
  名称：

  A Porphyrin Embedded in DNA

  摘要：

  Oligodeoxynucleotides containing an alkylporphyrin linked to the phosphate groups of DNA via oxypropyl chains have been synthesized. To our knowledge, these are the first porphyrin-nucleic acid conjugates bearing the porphyrin embedded in the backbone of DNA. Chain assembly was achieved by automated solid-phase synthesis using a dimethoxytrityl-protected porphyrin phosphoramidite and standard DNA building blocks. The thermal stability of duplexes involving the octadecamer 5'-CGCGCCTTC-P-CATTGCGG-3', where -P- denotes the porphyrin, was found to depend on the sequence of the complementary strand., A duplex where a thymidine residue in the complementary strand faces the porphyrin gives a higher melting point than duplexes bearing an abasic site or a dT(3) loop at this position. Duplex formation is accompanied by 180% hypochromicity at 501 nm, and other spectral changes unprecedented in porphyrinoids interacting with nucleic acids. Footprinting with nuclease S1, together with CD spectropolarimetry, indicates that the alkylporphyrin is embedded in a B-type duplex, with highly nuclease-sensitive phosphates only in the local environment of the porphyrin. Peak shifts in the NMR spectrum of the porphyrin-containing duplex, together with. fluorescence data, point toward an interaction between the porphyrin and the stacked nucleobases. Porphyrin-containing DNA-and RNA-duplexes, conveniently prepared with the porphyrin phosphoramidite described here, are expected to be valuable for photochemical and electron-transfer studies, as well as potential cofactor-using nucleic acid-based enzymes which could have had a role in prebiotic evolution.

  DOI：

  10.1021/jo9718051

文献信息

• A Porphyrin Embedded in DNA
  作者：Kurt Berlin、Rishi K. Jain、Matthew D. Simon、Clemens Richert

  DOI：10.1021/jo9718051

  日期：1998.3.1

  Oligodeoxynucleotides containing an alkylporphyrin linked to the phosphate groups of DNA via oxypropyl chains have been synthesized. To our knowledge, these are the first porphyrin-nucleic acid conjugates bearing the porphyrin embedded in the backbone of DNA. Chain assembly was achieved by automated solid-phase synthesis using a dimethoxytrityl-protected porphyrin phosphoramidite and standard DNA building blocks. The thermal stability of duplexes involving the octadecamer 5'-CGCGCCTTC-P-CATTGCGG-3', where -P- denotes the porphyrin, was found to depend on the sequence of the complementary strand., A duplex where a thymidine residue in the complementary strand faces the porphyrin gives a higher melting point than duplexes bearing an abasic site or a dT(3) loop at this position. Duplex formation is accompanied by 180% hypochromicity at 501 nm, and other spectral changes unprecedented in porphyrinoids interacting with nucleic acids. Footprinting with nuclease S1, together with CD spectropolarimetry, indicates that the alkylporphyrin is embedded in a B-type duplex, with highly nuclease-sensitive phosphates only in the local environment of the porphyrin. Peak shifts in the NMR spectrum of the porphyrin-containing duplex, together with. fluorescence data, point toward an interaction between the porphyrin and the stacked nucleobases. Porphyrin-containing DNA-and RNA-duplexes, conveniently prepared with the porphyrin phosphoramidite described here, are expected to be valuable for photochemical and electron-transfer studies, as well as potential cofactor-using nucleic acid-based enzymes which could have had a role in prebiotic evolution.