Fmoc-Asn(Trt)-OH | 1286441-72-2

• 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: Fmoc-Asn(Trt)-OH
• 英文别名: 9H-fluoren-9-ylmethyl N-[(3S)-1,4-dioxo-1-(tritylamino)pentan-3-yl]carbamate
• CAS: 1286441-72-2
• 化学式: C₃₉H₃₄N₂O₄
• 分子量: 594.71
• InChiKey: SRBGMXDOAHWKQH-BHVANESWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Fmoc-L-Pro Wang resin 、 Fmoc-Asn(Trt)-OH 、 Fmoc-甘氨酸 、 Fmoc-L-苯丙氨酸 、 FMOC-O-叔丁基-L-丝氨酸 、 Fmoc-O-叔丁基-L-苏氨酸 、 Fmoc-N-三苯甲基-L-谷氨酰胺 、 N-乙酰甘氨酸 在 哌啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Promising General Solution to the Problem of Ligating Peptides and Glycopeptides

  摘要：

  Our global goal is that of synthesizing complex polypeptides and glycopeptides in homogeneous form. Chemistry-derived access to homogeneous biologics could well have useful consequences in the discovery of drugs and vaccines. The key finding in this study is that thio acids can become highly competent acyl donors following even trace levels of oxidative activation, thereby undergoing amide bond formation upon reaction with N-terminal peptides. Though our data set does not establish the specific mechanism of this reaction, a framework to account for the fact that minute levels of oxidation actuate amide bond formation with high turnover is offered. An apparently general coupling of thio acids (including complex peptide thio acids with N-termini of complex peptides) has thus been realized. These ligations are conducted with minimal alpha-epimerization in the C-terminal group and allow for the coupling of N-terminal and C-terminal glycopeptides en route to homogeneous glycoproteins.

  DOI：

  10.1021/ja1084628

文献信息

• Display Selection of a Hybrid Foldamer–Peptide Macrocycle
  作者：Sebastian Dengler、Ryan T. Howard、Vasily Morozov、Christos Tsiamantas、Wei‐En Huang、Zhiwei Liu、Christopher Dobrzanski、Vojislava Pophristic、Sophie Brameyer、Céline Douat、Hiroaki Suga、Ivan Huc

  DOI：10.1002/anie.202308408

  日期：2023.11.13

  Expanding the chemical diversity of peptide macrocycle libraries for display selection is desirable to improve their potential to bind biomolecular targets. We now have implemented a considerable expansion through a large aromatic helical foldamer inclusion. A foldamer was first identified that undergoes flexizyme‐mediated tRNA acylation and that is capable of initiating ribosomal translation with yields sufficiently high to perform an mRNA display selection of macrocyclic foldamer–peptide hybrids. A hybrid macrocyclic nanomolar binder to the C‐lobe of the E6AP HECT domain was selected that showed a highly converged peptide sequence. A crystal structure and molecular dynamics simulations revealed that both the peptide and foldamer are helical in an intriguing reciprocal stapling fashion. The strong residue convergence could be rationalized based on their involvement in specific interactions with the target protein. The foldamer stabilizes the peptide helix through stapling and through contacts with key residues. These results altogether represent a significant extension of the chemical space amenable to display selection and highlight possible benefits of inserting an aromatic foldamer into a peptide macrocycle for the purpose of protein recognition.

  摘要扩大用于显示选择的多肽大循环文库的化学多样性是提高其与生物分子靶标结合潜力的理想选择。现在，我们通过包含一个大型芳香族螺旋折叠体实现了相当大的扩展。我们首先发现了一种折叠聚合体，这种聚合体能进行柔性酶介导的 tRNA酰化，并能启动核糖体翻译，其产量足以对大环折叠聚合体-肽杂交体进行 mRNA 展示选择。筛选出的与 E6AP HECT 结构域 C-lobe 结合的纳摩尔级大环混合体显示出高度趋同的肽序列。晶体结构和分子动力学模拟显示，肽和折叠器都是螺旋形的，呈有趣的互订方式。由于这些残基参与了与目标蛋白质的特异性相互作用，因此可以合理地解释这种强烈的残基趋同性。折叠聚合物通过订书以及与关键残基的接触来稳定肽螺旋。这些结果共同代表了可用于显示选择的化学空间的重大扩展，并凸显了将芳香族折叠器插入肽大环以实现蛋白质识别的可能益处。
• LYSOBACTINAMIDE
  申请人：AiCuris GmbH & Co. KG

  公开号：EP2007794B1

  公开（公告）日：2011-09-14
• [DE] LYSOBACTINAMIDE<br/>[EN] LYSOBACTIN AMIDES<br/>[FR] LYSOBACTINAMIDE
  申请人：AICURIS GMBH & CO KG

  公开号：WO2007118691A1

  公开（公告）日：2007-10-25

  [EN] The invention relates to lysobactin amides, methods for the production thereof, and the use thereof for producing medicaments utilized for treating and/or preventing diseases, particularly bacterial infectious diseases.
  [FR] L'invention concerne un lysobactinamide et son procédé de préparation, ainsi que son utilisation pour la production de médicaments destinés au traitement et/ou à la prophylaxie de maladies, en particulier de maladies infectieuses bactériennes.
  [DE] Die Erfindung betrifft Lysobactinamide und Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Herstellung von Arzneimitteln zur Behandlung und/oder Prophylaxe von Krankheiten, insbesondere bakteriellen Infektionskrankheiten.