N-Boc-4-amino-pyrrole-2-carboxylic acid methyl ester | 210298-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-Boc-4-amino-pyrrole-2-carboxylic acid methyl ester
• 英文别名: methyl 4-(tert-butoxycarbonyl)aminopyrrole-2-carboxylate；methyl 4-[(2-methylpropan-2-yl)oxycarbonylamino]-1H-pyrrole-2-carboxylate
• CAS: 210298-48-9
• 化学式: C₁₁H₁₆N₂O₄
• 分子量: 240.259
• InChiKey: QNOADFQHLRFJIC-UHFFFAOYSA-N

物化性质

• 沸点：
  338.1±27.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Boc-4-amino-pyrrole-2-carboxylic acid methyl ester 在 palladium on activated charcoal 氢氧化钾 、 水 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙酸乙酯 、 丙酮 为溶剂， 45.0 ℃ 、1.03 MPa 条件下， 反应 62.0h， 生成 1,4-bis[N,N'-4-[(tert-butoxycarbonyl)amino]pyrrolyl-2-carboxylic acid]butane
  参考文献：
  名称：

  A Comparison of H-Pin and Hairpin Polyamide Motifs for the Recognition of the Minor Groove of DNA

  摘要：

  In order to compare strategies for covalent linkage of pyrrole-imidazole (Py-Im) polyamide subunits, equilibrium association constants (K-a) were determined for a series of polyamides coupled either C-N with a gamma-aminobutyric acid linker (hairpin motif) or linked across a central Py/Py pair through a tetramethylene spacer (H-pin motif). Compared to the well-characterized hairpin motif, the H-pin motif represents a unique and relatively unexplored approach for increasing the affinity and the specificity of 2:1 polyamide-DNA complexes. Three H-pin polyamides containing six or 10 aromatic amino acid residues were synthesized by solid-phase methods using a Boc-protected bispyrrole monomer combined with bi-directional synthesis. The DNA-binding properties of six-ring and 10-ring H-pin polyamides were analyzed by quantitative DNase I footprint titration on a DNA fragment containing five or seven base pair match and mismatch sequences, respectively. The homodimeric H-Pin (ImPyPy-beta-Dp)(2)C-4 (site of the tetramethylene linker indicated in bold type) binds to the seven base pair match sequence 5'-TGTCA-3' with K-a = 9.3 x 10(6) M-1 and 9.4-fold specificity relative to the single base mismatch sequence 5'-TGT (T) under bar A-3' (K-a = 9.9 x 10(6) M-1). The heterodimeric H-Pin (ImPyPy-beta-Dp)C-4(AcPyPyPy-beta-Dp) binds a 5'-TGTTA-3' match sequence with K-a = 2.0 x 10(6) M-1 and 3.5-fold specificity versus the single base mismatch sequence 5'-TGT (C) under bar A-3' (K-a = 5.7 x 10(5) M-1). The 10-ring H-pin (ImPyPyPyPy-beta-Dp)(2)C-4 binds to the seven base pair match sequence 5'-TGTAACA-3' with K-a = 4.4 x 10(8) M-1 and 28-fold specificity versus the single base pair mismatch sequence 5'-TG (G) under bar AACA-3' (K-a = 1.6 x 10(7) M-1). We find that H-pin polyamides bind with four- to 180-fold enhanced affinity and two- to 10-fold enhanced specificity relative to unlinked analogues, but with 25- to 150-fold reduced affinity and approximately one- to 20-fold reduced specificity compared to the corresponding hairpin polyamides. These results indicate that H-pin polyamides represent a viable motif for the recognition of predetermined sequences in the DNA minor groove; however, DNA-binding properties appear inferior to the corresponding hairpins.

  DOI：

  10.1002/(sici)1521-3765(19980515)4:5<796::aid-chem796>3.0.co;2-g
• 作为产物：
  描述：

  甲基 4-醛基-1H-吡咯-2-甲酸酯 在 sodium chlorite 、 sodium dihydrogenphosphate 、 叠氮磷酸二苯酯 、 双氧水 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 N-Boc-4-amino-pyrrole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and characterization of Boc-protected 4-amino- and 5-amino-pyrrole-2-carboxylic acid methyl esters

  摘要：

  Syntheses of Boc-protected 4-amino- and 5-amino-pyrrole-2-carboxylic acid methyl esters have been achieved and the structures of these compounds have been fully characterized by detailed NMR studies. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.135

文献信息

• DNA Interstrand Crosslinks by H-pin Polyamide (<i>S</i> )<i>-seco</i> -CBI Conjugates
  作者：Chuanxin Guo、Sefan Asamitsu、Gengo Kashiwazaki、Shinsuke Sato、Toshikazu Bando、Hiroshi Sugiyama

  DOI：10.1002/cbic.201600425

  日期：2017.1.17

  Conjugates and crosslinks: H‐pin imidazole‐pyrrole polyamide seco‐CBI conjugates that can be used to form sequence‐specific DNA interstrand crosslinks (ICLs) have been synthesized. One conjugate, which contained a chiral (S)‐seco‐CBI moiety, exhibited the highest sequence‐specific ICL activity toward the target DNA sequence and was cytotoxic to a cancer cell line.

  缀合物和交联：已合成了可用于形成序列特异性DNA链间交联（ICL）的H-pin咪唑-吡咯聚酰胺seco - CBI缀合物。一种包含手性（S）-seco- CBI部分的缀合物，对目标DNA序列表现出最高的序列特异性ICL活性，并对癌细胞系具有细胞毒性。
• Detection of triplet repeat sequences in the double-stranded DNA using pyrene-functionalized pyrrole–imidazole polyamides with rigid linkers
  作者：Jun Fujimoto、Toshikazu Bando、Masafumi Minoshima、Shinsuke Uchida、Makoto Iwasaki、Ken-ichi Shinohara、Hiroshi Sugiyama

  DOI：10.1016/j.bmc.2008.04.060

  日期：2008.6

  Methods for sequence-specific detection in double-stranded DNA (dsDNA) are becoming increasingly useful and important as diagnostic and imaging tools. Recently, we designed and synthesized pyrrole (Py)-imidazole (Im) polyamides possessing two pyrene moieties, 1, which showed an increased excimer emission in the presence of (CAG)(12)-containing oligodeoxynucleotides (ODN) 1 and 2. In this study, we synthesized bis-pyrenyl Py-Im polyamides with rigid linkers 2, 3, and 4 to improve their fluorescence properties. Among the conjugates, 2 showed a marked increase in excimer emission, which was dependent on the concentration of the target ODN and the number of CAG repeats in the dsDNA. Unlike conjugate 1, which has flexible linkers, the excimer emission intensity of 2 was retained at over 85%, even after 4 h. Py-Im polyamides have the potential to be important diagnostic molecules for detecting genetic differences between individuals. (C) 2008 Elsevier Ltd. All rights reserved.