Ac-(cyclo-o,m)-[F(Aib)AAF]-NH2 | 1364707-88-9

• 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: Ac-(cyclo-o,m)-[F(Aib)AAF]-NH2
• 英文别名: (9S,15S,18S,21S)-9-acetamido-12,12,15,18-tetramethyl-10,13,16,19-tetraoxo-11,14,17,20-tetrazatricyclo[21.3.1.02,7]heptacosa-1(26),2,4,6,23(27),24-hexaene-21-carboxamide
• CAS: 1364707-88-9
• 化学式: C₃₀H₃₈N₆O₆
• 分子量: 578.668
• InChiKey: KBGVJOCWNZHQPO-KTIFSJKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  42
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  189
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (9S,12S,15S,18S,21S)-9-acetamido-15-(4-aminobutyl)-12,18-dimethyl-10,13,16,19-tetraoxo-11,14,17,20-tetrazatricyclo[21.3.1.02,7]heptacosa-1(26),2,4,6,23(27),24-hexaene-21-carboxamide 、 乙酸酐 在 三氟乙酸 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以7.6 mg的产率得到Ac-(cyclo-o,m)-[F(Aib)AAF]-NH2
  参考文献：
  名称：

  Biaryl-Bridged Macrocyclic Peptides: Conformational Constraint via Carbogenic Fusion of Natural Amino Acid Side Chains

  摘要：

  A general method for constraining peptide conformations via linkage of aromatic sidechains has been developed. Macrocydization of suitably functionalized tri-, tetra- and pentapeptides via Suzuki-Miyaura cross-coupling has been used to generate side chain to side chain, biaryl-bridged 14- to 21-membered macrocyclic peptides. Biaryl bridges possessing three different configurations, meta-meta, meta-ortho, and ortho-meta, were systematically explored through regiochemical variation of the aryl halide and aryl boronate coupling partners, allowing fine-tuning of the resultant macrocycle conformation. Suzuki-Miyaura macrocyclizations were successfully achieved both in solution and on solid phase for all three sizes of peptide. This approach constitutes a means of constraining peptide conformation via direct carbogenic fusion of side chains of naturally occurring amino acids such as phenylalanine and tyrosine, and so is complementary to strategies involving non-natural, for example, hydrocarbon, bridges.

  DOI：

  10.1021/jo202105v