phenyl (4-(tert-butyldimethylsilyloxy)benzyloxy)formate | 1052677-15-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl (4-(tert-butyldimethylsilyloxy)benzyloxy)formate
• CAS: 1052677-15-2
• 化学式: C₂₀H₂₆O₄Si
• 分子量: 358.51
• InChiKey: NRJUNQVXJNFDRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  phenyl (4-(tert-butyldimethylsilyloxy)benzyloxy)formate 、 乙二胺 以 乙醇 为溶剂， 以54%的产率得到N-(4-OTBS-Cbz) ethylenediamine
  参考文献：
  名称：

  扩展 PNA 合成的范围和正交性

  摘要：

  根据 Watson 和 Crick 碱基配对规则，肽核酸 (PNA) 与天然寡核苷酸杂交。PNA 寡聚体的稳健性和易于合成使它们成为一个有吸引力的平台，用于编码小分子或大分子，用于微阵列目的和其他基于可编程自组装的应用。这些努力的基石是 PNA 合成与其他化学物质的正交性。在此，我们对末端氮原子的六种保护基团（Alloc、Teoc、4-N3Cbz、Fmoc、4-OTBSCbz 和 Azoc）和核碱基上的五种保护基团（Cl-Bhoc、F- Bhoc、Teoc、4-OMeCbz 和 Boc）。

  DOI：

  10.1002/ejoc.200800141
• 作为产物：
  描述：

  氯甲酸苯酯 、 4-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧基]-苯甲醇 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以100%的产率得到phenyl (4-(tert-butyldimethylsilyloxy)benzyloxy)formate
  参考文献：
  名称：

  扩展 PNA 合成的范围和正交性

  摘要：

  根据 Watson 和 Crick 碱基配对规则，肽核酸 (PNA) 与天然寡核苷酸杂交。PNA 寡聚体的稳健性和易于合成使它们成为一个有吸引力的平台，用于编码小分子或大分子，用于微阵列目的和其他基于可编程自组装的应用。这些努力的基石是 PNA 合成与其他化学物质的正交性。在此，我们对末端氮原子的六种保护基团（Alloc、Teoc、4-N3Cbz、Fmoc、4-OTBSCbz 和 Azoc）和核碱基上的五种保护基团（Cl-Bhoc、F- Bhoc、Teoc、4-OMeCbz 和 Boc）。

  DOI：

  10.1002/ejoc.200800141

文献信息

• FRET-based assay of the processing reaction kinetics of stimulus-responsive peptides: influence of amino acid sequence on reaction kinetics
  作者：Akira Shigenaga、Jun Yamamoto、Hiroko Hirakawa、Keiko Yamaguchi、Akira Otaka

  DOI：10.1016/j.tet.2009.01.063

  日期：2009.3

  study, we developed a FRET-based assay system to estimate the kinetics of the stimulus-induced processing (peptide bond cleavage) reaction. Based on the FRET system, it was clarified that introduction of a sterically less-hindered or polar residue at the position adjacent to the stimulus-responsive amino acid accelerates the processing reaction.

  在化学生物学领域中，通过刺激来控制肽基功能的方法引起了越来越多的关注。最近，我们报道了一种刺激反应性肽，暴露于刺激后可以裂解。在这项研究中，我们开发了一种基于FRET的测定系统，以评估刺激诱导的加工（肽键裂解）反应的动力学。基于FRET系统，澄清了在与刺激响应性氨基酸相邻的位置处引入空间较少受阻或极性的残基加速了加工反应。
• Biotin Ergopeptide Probes for Dopamine Receptors
  作者：Marc Vendrell、Anabel Molero、Sergio González、Kamil Pérez-Capote、Carme Lluis、Peter J. McCormick、Rafael Franco、Antoni Cortés、Vicent Casadó、Fernando Albericio、Miriam Royo

  DOI：10.1021/jm101566d

  日期：2011.2.24

  The incorporation of chemical modifications into the structure of bioactive compounds is often difficult because the biological properties of the new molecules must be retained with respect to the native ligand. Ergopeptides, with their high affinities at D-1 and D-2 dopamine receptors, are particularly complex examples. Here, we report the systematic derivatization of two ergopeptides with different peptide-based spacers and their evaluation by radioligand binding assays. Selected spacer-containing ergopeptides with minimal biological alteration and a proper anchoring point were further derivatized with a biotin reporter. Detailed characterization studies identified 13 as a biotin ergopeptide maintaining high affinity and agonist behavior at dopamine receptors, being a useful tool for the study of heteromers involving D1R, D2R, or D3R.
• Discovery of Targeting Ligands for Breast Cancer Cells Using the One-Bead One-Compound Combinatorial Method
  作者：Nianhuan Yao、Wenwu Xiao、Xiaobing Wang、Jan Marik、See Hyoung Park、Yoshikazu Takada、Kit S. Lam

  DOI：10.1021/jm801062d

  日期：2009.1.8

  Four "one-bead one-compound" (OBOC combinatorial libraries were designed, synthesized, and screened against MDA-MB-231 breast cancer cells. A novel cyclic peptide 1 (LXY1) with high binding specificity C) C to 0 integrin was identified. Molecular interactions between 0 integrin and I were characterized by using a series of K562 cells transfected with various mutant alpha 3 integrins. Using analytic flow cytometry, the binding affinity (K-d) of 1 to alpha 3 integrin on MDA-MB-231 breast cancer cells was determined to be approximately 0.4 mu M. Based on the established structure-activity relationship (SAR) study, two highly focused cyclic peptide libraries were further designed, synthesized, and screened against MDA-MB-231 breast cancer cells under stringent conditions. A novel cyclic peptide 2 (LXY3) with a high binding affinity (IC50 = 57 nM) was identified. Moreover, the targeting efficiency and specificity of 2 to the breast adenocarcinoma tumors in mouse xenografts were further confirmed by in vivo and ex vivo near-infrared fluorescence optical imaging.
• Development of bestatin-based activity-based probes for metallo-aminopeptidases
  作者：Michael B. Harbut、Geetha Velmourougane、Gilana Reiss、Rajesh Chandramohanadas、Doron C. Greenbaum

  DOI：10.1016/j.bmcl.2008.09.021

  日期：2008.11

  A novel set of activity-based probes (ABPs) for functionally pro. ling metallo-aminopeptidases was synthesized based on the bestatin inhibitor scaffold, the first synthesis of bestatin analogues using solid-phase techniques. These ABPs were shown to label metallo-aminopeptidases, using both a biotin and a fluorophore reporter, in an activity-dependent manner. This probe class was also shown to be amenable to 'click' chemistry labeling for possible use in live cells. Finally, we demonstrate that the ABPs are able to label an aminopeptidase in a complex proteome. Thus, these bestatin-based probes should have wide utility to functionally profile aminopeptidases in many biological systems. (C) 2008 Elsevier Ltd. All rights reserved.