HO-Pro-Oxazole-Thiazole-Pro-D-Phe-NHBoc | 1453168-05-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: HO-Pro-Oxazole-Thiazole-Pro-D-Phe-NHBoc
• CAS: 1453168-05-2
• 化学式: C₃₀H₃₅N₅O₇S
• 分子量: 609.703
• InChiKey: OAPXEEOYVCWEAM-OIBXWCBGSA-N

物化性质

• 密度：
  1.350±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  155.17
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  HO-Pro-Oxazole-Thiazole-Pro-D-Phe-NHBoc 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 HO-Thiazole-Ala-Val-Pro-Oxazole-Thiazole-Pro-D-Phe-NHBoc
  参考文献：
  名称：

  Synthesis, Structure–Activity Analysis, and Biological Evaluation of Sanguinamide B Analogues

  摘要：

  We report the first synthesis of sanguinamide B analogues. Substituting N-methylated (N-Me) amino acids, glycine (Gly), and L- or D-phenylalanine (Phe) into the backbone of sanguinamide B showed that only L- and D-Phe residues controlled the macrocycle conformation. The N-methylated and glycine analogues all had multiple conformations, whereas the L- and D-Phe derivatives only had a single conformation. Testing of all conformer analogues showed that inclusion of an L- or D-Phe was a superior design element than incorporating the N-Me moiety that is often utilized to control macrocyclic conformation. Finally, we show that there is an ideal Phe residue (in this case L-Phe) for generating compounds that have the greatest inhibitory effect on bacterial motility. Our data support the hypothesis that the macrocyclic conformation is dictated by the benzyl moiety requiring a "pseudoequatorial" position, and all other energy considerations are secondary.

  DOI：

  10.1021/jo3017499
• 作为产物：
  描述：

  MeO-Oxazole-Thiazole-Pro-NH 在 lithium hydroxide monohydrate 、 双氧水 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 HO-Pro-Oxazole-Thiazole-Pro-D-Phe-NHBoc
  参考文献：
  名称：

  Synthesis of macrocycles that inhibit protein synthesis: stereochemistry and structural based studies on sanguinamide B derivatives

  摘要：

  DOI：

  10.1016/j.tetlet.2014.10.089

文献信息

• Mechanistic Studies of Sanguinamide B Derivatives: A Unique Inhibitor of Eukaryotic Ribosomes
  作者：Worawan Tantisantisom、Deborah M. Ramsey、Shelli R. McAlpine

  DOI：10.1021/ol401749p

  日期：2013.9.20

  Described are mechanistic studies of two Sanguinamide B (San B) derivatives. These compounds were identified as eukaryotic ribosomal inhibitors. Two biotinylated San B derivatives were synthesized and used to capture protein targets in a pull-down assay. LC/MS/MS analysis of the San B-captured targets identified several proteins that comprise eukaryotic ribosomal subunits. The translation inhibitory effect of San B was confirmed using an in vitro translation assay. Moreover, an evaluation of cell death mechanisms is reported.