Fmoc-[γ-N(alloc)-propyl]Gly-OH | 174800-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-[γ-N(alloc)-propyl]Gly-OH
• 英文别名: N-Fmoc-(N-(Alloc)3-aminopropyl)glycine；Fmoc-N-Aminopropyl-Gly(Alloc)-OH；2-[9H-fluoren-9-ylmethoxycarbonyl-[3-(prop-2-enoxycarbonylamino)propyl]amino]acetic acid
• CAS: 174800-19-2
• 化学式: C₂₄H₂₆N₂O₆
• 分子量: 438.48
• InChiKey: OKXJIBZFWCIAGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Rink amide resin 、 Fmoc-[γ-N(alloc)-propyl]Gly-OH 在 2,4,6-三甲基吡啶 、 三光气 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Novel Urea Bridged Macrocyclic Molecules Using BTC

  摘要：

  Cyclic ureas have interesting pharmacological properties that have led to their use as analogs of bioactive compounds. Several synthetic routes for urea formation by cyclization of diamines are known, based on the nucleophilic reaction of the amines with phosgene or phosgene derivatives. We have developed a procedure for a triphosgene mediated, on-resin urea cyclization. Four novel urea macrocyclic molecules were synthesized in order to demonstrate the feasibility of this method.

  DOI：

  10.3987/com-07-s(u)40
• 作为产物：
  描述：

  、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 三乙胺 、 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 Fmoc-[γ-N(alloc)-propyl]Gly-OH
  参考文献：
  名称：

  使用新的Alloc保护的甘氨酸构建单元合成尿素主链环状肽的新方法。

  摘要：

  利用用作天然药效基团的官能团对生物活性肽的环化通常伴随着活性的丧失。开发了骨架环化方法以克服该限制并增强药理特性。骨干环肽是通过掺入能够形成酰胺，二硫键和配位键的特殊结构单元来制备的。尿素桥通常用于通过连接两个胺官能化的侧链来制备环肽。在这里，我们介绍了尿素骨架环化作为制备骨架环肽文库的另一种方法。用于结晶的Fmoc-合成的直接方法Ñ α介绍了[ω-氨基（Alloc）-烷基]甘氨酸构建单元。制备了一组尿素主链环状糖原合酶激酶3类似物，并评估了其作为抗癌药对蛋白激酶B的抑制作用。版权所有©2010欧洲肽协会和John Wiley＆Sons，Ltd.。

  DOI：

  10.1002/psc.1218

文献信息

• Cyclic peptide inhibitors of HIV-1 integrase derived from the LEDGF/p75 protein
  作者：Zvi Hayouka、Mattan Hurevich、Aviad Levin、Hadar Benyamini、Anat Iosub、Michal Maes、Deborah E. Shalev、Abraham Loyter、Chaim Gilon、Assaf Friedler

  DOI：10.1016/j.bmc.2010.09.046

  日期：2010.12

  Restricting linear peptides to their bioactive conformation is an attractive way of improving their stability and activity. We used a cyclic peptide library with conformational diversity for selecting an active and stable peptide that mimics the structure and activity of the HIV-1 integrase (IN) binding loop from its cellular cofactor LEDGF/p75 (residues 361-370). All peptides in the library had the same primary sequence, and differed only in their conformation. Library screening revealed that the ring size and linker structure had a huge effect on the conformation, binding and activity of the peptides. One of the cyclic peptides, c(MZ 4-1), was a potent and stable inhibitor of IN activity in vitro and in cells even after 8 days. The NMR structure of c(MZ 4-1) showed that it obtains a bioactive conformation that is similar to the parent site in LEDGF/p75. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of Novel Urea Bridged Macrocyclic Molecules Using BTC
  作者：Mattan Hurevich、Yaniv Barda、Chaim Gilon

  DOI：10.3987/com-07-s(u)40

  日期：——

  Cyclic ureas have interesting pharmacological properties that have led to their use as analogs of bioactive compounds. Several synthetic routes for urea formation by cyclization of diamines are known, based on the nucleophilic reaction of the amines with phosgene or phosgene derivatives. We have developed a procedure for a triphosgene mediated, on-resin urea cyclization. Four novel urea macrocyclic molecules were synthesized in order to demonstrate the feasibility of this method.
• Novel method for the synthesis of urea backbone cyclic peptides using new Alloc-protected glycine building units
  作者：Mattan Hurevich、Yftah Tal-Gan、Shoshana Klein、Yaniv Barda、Alexander Levitzki、Chaim Gilon

  DOI：10.1002/psc.1218

  日期：2010.4

  properties. Backbone cyclic peptides are prepared by the incorporation of special building units, capable of forming amide, disulfide and coordinative bonds. Urea bridge is often used for the preparation of cyclic peptides by connecting two amine functionalized side chains. Here we present urea backbone cyclization as an additional method for the preparation of backbone cyclic peptide libraries. A

  利用用作天然药效基团的官能团对生物活性肽的环化通常伴随着活性的丧失。开发了骨架环化方法以克服该限制并增强药理特性。骨干环肽是通过掺入能够形成酰胺，二硫键和配位键的特殊结构单元来制备的。尿素桥通常用于通过连接两个胺官能化的侧链来制备环肽。在这里，我们介绍了尿素骨架环化作为制备骨架环肽文库的另一种方法。用于结晶的Fmoc-合成的直接方法Ñ α介绍了[ω-氨基（Alloc）-烷基]甘氨酸构建单元。制备了一组尿素主链环状糖原合酶激酶3类似物，并评估了其作为抗癌药对蛋白激酶B的抑制作用。版权所有©2010欧洲肽协会和John Wiley＆Sons，Ltd.。