| 872045-50-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• CAS: 872045-50-6
• 化学式: C₅₂H₅₈N₂₀O₁₁
• 分子量: 1139.16
• InChiKey: PERLBPLZRCWAGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  83.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  377.31
• 氢给体数：
  10.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  N,N-二甲基-1,3-二氨基丙烷 、 生成 N-[2-[[5-[[4-[[5-[[5-[[5-[[5-[[3-[3-(dimethylamino)propylamino]-3-oxopropyl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]amino]-4-oxobutyl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylimidazol-4-yl]-1-methyl-4-[(1-methylimidazole-2-carbonyl)amino]imidazole-2-carboxamide
  参考文献：
  名称：

  Recognition of a 5‘-(A,T)GGG(A,T)₂-3‘ Sequence in the Minor Groove of DNA by an Eight-Ring Hairpin Polyamide

  摘要：

  The use of pyrrole-imidazole polyamides for the recognition of core 5'-GGG-3' sequences in the minor groove of double stranded DNA is described. Two hairpin pyrrole-imidazole polyamides, ImImIm-gamma-PyPyPy-beta-Dp and ImImImPy-gamma-PyPyPyPy-beta-Dp (Im = N-methylimidazole-2-carboxamide, Py = N-methylpyrrole-2-carboxamide, beta = p-alanine, gamma = gamma-aminobutyric acid, and Dp = ((dimethylamino)propyl)amide), as well as the corresponding EDTA affinity cleaving derivatives, were synthesized and their DNA binding properties analyzed. Quantitative DNase I footprint titrations demonstrate that ImImIm-gamma-PyPyPy-beta-Dp binds the formal match sequence 5'-AGGGA-3' with an equilibrium association constant of K-a = 5 x 10(6) M(-1) (10 mM Tris . HCl, 10 mM KCl, 10 mM MgCl2, and 5 mM CaCl2, pH 7.0 and 22 degrees C). ImImImPy-gamma-PyPyPyPy-beta-Dp binds the same site, 5'-AGGGAA-3', approximately two orders of magnitude more tightly than the six ring polyamide, with an equilibrium association constant of K-a = 4 x 10(8) M(-1). The eight-ring hairpin polyamide demonstrates greater specifity for single base pair mismatches than does the six ring hairpin. Polyamides with an EDTA . Fe(II) moiety at the carboxy terminus confirm that each hairpin binds in a single orientation. The high affinity recognition of a 5'-GGG-3' core sequence by an eight ring polyamide containing three contiguous imidazole amino acids demonstrates the versatility of pyrrole-imidazole polyamides and broadens the sequence repertoire for DNA recognition.

  DOI：

  10.1021/ja9611598
• 作为产物：
  描述：

  1-甲基-1H-咪唑-2-羧酸 、 Boc-beta-丙氨酸 、 4-叔丁氧羰基氨基-1-甲基-1H-咪唑-2-甲酸 、 4-叔丁氧羰氨基-1-甲基-1H-吡咯-2-苯并噻唑羧酸甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 生成
  参考文献：
  名称：

  Recognition of a 5‘-(A,T)GGG(A,T)₂-3‘ Sequence in the Minor Groove of DNA by an Eight-Ring Hairpin Polyamide

  摘要：

  The use of pyrrole-imidazole polyamides for the recognition of core 5'-GGG-3' sequences in the minor groove of double stranded DNA is described. Two hairpin pyrrole-imidazole polyamides, ImImIm-gamma-PyPyPy-beta-Dp and ImImImPy-gamma-PyPyPyPy-beta-Dp (Im = N-methylimidazole-2-carboxamide, Py = N-methylpyrrole-2-carboxamide, beta = p-alanine, gamma = gamma-aminobutyric acid, and Dp = ((dimethylamino)propyl)amide), as well as the corresponding EDTA affinity cleaving derivatives, were synthesized and their DNA binding properties analyzed. Quantitative DNase I footprint titrations demonstrate that ImImIm-gamma-PyPyPy-beta-Dp binds the formal match sequence 5'-AGGGA-3' with an equilibrium association constant of K-a = 5 x 10(6) M(-1) (10 mM Tris . HCl, 10 mM KCl, 10 mM MgCl2, and 5 mM CaCl2, pH 7.0 and 22 degrees C). ImImImPy-gamma-PyPyPyPy-beta-Dp binds the same site, 5'-AGGGAA-3', approximately two orders of magnitude more tightly than the six ring polyamide, with an equilibrium association constant of K-a = 4 x 10(8) M(-1). The eight-ring hairpin polyamide demonstrates greater specifity for single base pair mismatches than does the six ring hairpin. Polyamides with an EDTA . Fe(II) moiety at the carboxy terminus confirm that each hairpin binds in a single orientation. The high affinity recognition of a 5'-GGG-3' core sequence by an eight ring polyamide containing three contiguous imidazole amino acids demonstrates the versatility of pyrrole-imidazole polyamides and broadens the sequence repertoire for DNA recognition.

  DOI：

  10.1021/ja9611598

文献信息

• Sequence-Specific Fluorescence Detection of DNA by Polyamide−Thiazole Orange Conjugates
  作者：Eric J. Fechter、Bogdan Olenyuk、Peter B. Dervan

  DOI：10.1021/ja054650k

  日期：2005.11.30

  Fluorescent methods to detect specific double-stranded DNA sequences without the need for denaturation may be useful in the field of genetics. Three hairpin pyrrole-imidazole polyamides 2-4 that target their respective sequences 5'-WGGGWW-3', 5'-WGGCCW-3', and 5'-WGWWCW-3'(W = A or T) were conjugated to thiazole orange dye at the C-termini to examine their fluorescence properties in the presence and absence of match duplex DNA. The conjugates fluoresce weakly in the absence of DNA but showed significant enhancement (> 1000-fold) upon the addition of 1 equiv of match DNA and only slight enhancement with the addition of mismatch DNA. The polyamide-dye conjugates bound specific DNA sequences with high affinity (K-a > 10(8) M-1) and unwound the DNA duplex through intercalation (unwinding angle, Phi, similar to 8 degrees). This new class of polyamides provides a method to specifically detect DNA sequences without denaturation.