benzyl 2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-(tritylamino)pentyl]amino]acetate | 1357080-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: benzyl 2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-(tritylamino)pentyl]amino]acetate
• CAS: 1357080-86-4
• 化学式: C₄₈H₄₅N₃O₅
• 分子量: 743.902
• InChiKey: KEBHRDBHJGOLOK-KDXMTYKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  56
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-(tritylamino)pentyl]amino]acetate 在 palladium 10% on activated carbon 、 氢气 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 2-[3-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]propanoyl-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-(tritylamino)pentyl]amino]acetic acid
  参考文献：
  名称：

  γ-AApeptides bind to RNA by mimicking RNA-binding proteins

  摘要：

  蛋白质与RNA之间的相互作用对许多细胞过程至关重要，包括RNA的转录和加工、翻译以及病毒感染。我们在这里报道一种γ-AA肽，它能够模拟HIV-1 Tat蛋白，并以纳摩尔亲和力结合HIV和BIV的TAR RNA，这一亲和力与Tat的RNA结合片段（氨基酸49-58）相当。该相互作用能抵抗大量tRNA的存在。由于对蛋白水解的抵抗以及无限的多样化潜力，γ-AA肽可能会成为调节RNA-蛋白相互作用的新型肽模仿物。

  DOI：

  10.1039/c1ob05738c
• 作为产物：
  描述：

  甘氨酸苄酯盐酸盐 、 N-α-Fmoc-N-γ-trityl-glutaminal 在 三乙胺 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.75h， 生成 benzyl 2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-(tritylamino)pentyl]amino]acetate
  参考文献：
  名称：

  γ-AApeptides bind to RNA by mimicking RNA-binding proteins

  摘要：

  蛋白质与RNA之间的相互作用对许多细胞过程至关重要，包括RNA的转录和加工、翻译以及病毒感染。我们在这里报道一种γ-AA肽，它能够模拟HIV-1 Tat蛋白，并以纳摩尔亲和力结合HIV和BIV的TAR RNA，这一亲和力与Tat的RNA结合片段（氨基酸49-58）相当。该相互作用能抵抗大量tRNA的存在。由于对蛋白水解的抵抗以及无限的多样化潜力，γ-AA肽可能会成为调节RNA-蛋白相互作用的新型肽模仿物。

  DOI：

  10.1039/c1ob05738c

文献信息

• DNA-Templated Polymerization of Side-Chain-Functionalized Peptide Nucleic Acid Aldehydes
  作者：Ralph E. Kleiner、Yevgeny Brudno、Michael E. Birnbaum、David R. Liu

  DOI：10.1021/ja0753997

  日期：2008.4.1

  The DNA-templated polymerization of synthetic building blocks provides a potential route to the laboratory evolution of sequence-defined polymers with structures and properties not necessarily limited to those of natural biopolymers. We previously reported the efficient and sequence-specific DNA-templated polymerization of peptide nucleic acid (PNA) aldehydes. Here, we report the enzyme-free, DNA-templated polymerization of side-chain-functionalized PNA tetramer and pentamer aldehydes. We observed that polymerization of tetramer and pentamer PNA building blocks with a single lysine-based side chain at various positions in the building block could proceed efficiently and sequence specifically. In addition, DNA-templated polymerization also proceeded efficiently and in a sequence-specific manner with pentamer PNA aldehydes containing two or three lysine side chains in a single building block to generate more densely functionalized polymers. To further our understanding of side-chain compatibility and expand the capabilities of this system, we also examined the polymerization efficiencies of 20 pentamer building blocks each containing one of five different side-chain groups and four different side-chain regio- and stereochemistries. Polymerization reactions were efficient for all five different side-chain groups and for three of the four combinations of side-chain regio- and stereochemistries. Differences in the efficiency and initial rate of polymerization correlate with the apparent melting temperature of each building block, which is dependent on side-chain regio- and stereochemistry but relatively insensitive to side-chain structure among the substrates tested. Our findings represent a significant step toward the evolution of sequence-defined synthetic polymers and also demonstrate that enzyme-free nucleic acid-templated polymerization can occur efficiently using substrates with a wide range of side-chain structures, functionalization positions within each building block, and functionalization densities.
• γ-AApeptides bind to RNA by mimicking RNA-binding proteins
  作者：Youhong Niu、Alisha “Jonesy” Jones、Haifan Wu、Gabriele Varani、Jianfeng Cai

  DOI：10.1039/c1ob05738c

  日期：——

  The interactions between proteins and RNAs are of vital importance for many cellular processes, including transcription and processing of RNA, translation, and viral infections. Here we report an γ-AApeptide that can mimic HIV-1 Tat protein and bind to TAR RNAs of HIV and BIV with nanomolar affinity, comparable to that of the RNA-binding fragment of Tat (amino acids 49–58). The interaction is resistant to the presence of a large excess of tRNA. With resistance to proteolytic hydrolysis and limitless potential for diversification, γ-AApeptides may emerge as a new class of peptidomimetics to modulate RNA-protein interactions.

  蛋白质与RNA之间的相互作用对许多细胞过程至关重要，包括RNA的转录和加工、翻译以及病毒感染。我们在这里报道一种γ-AA肽，它能够模拟HIV-1 Tat蛋白，并以纳摩尔亲和力结合HIV和BIV的TAR RNA，这一亲和力与Tat的RNA结合片段（氨基酸49-58）相当。该相互作用能抵抗大量tRNA的存在。由于对蛋白水解的抵抗以及无限的多样化潜力，γ-AA肽可能会成为调节RNA-蛋白相互作用的新型肽模仿物。