Ac-(cyclo-m,m)-[(3-Cl)FAAAY]-CO2Me | 1364706-18-2

• 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: Ac-(cyclo-m,m)-[(3-Cl)FAAAY]-CO2Me
• 英文别名: (m,m)-cyclo Ac-F(3-Cl)AAAY-CO2Me；methyl (8S,11S,14S,17S,20S)-20-acetamido-24-chloro-11,14,17-trimethyl-10,13,16,19-tetraoxo-3-phenylmethoxy-9,12,15,18-tetrazatricyclo[20.3.1.12,6]heptacosa-1(25),2,4,6(27),22(26),23-hexaene-8-carboxylate
• CAS: 1364706-18-2
• 化学式: C₃₇H₄₂ClN₅O₈
• 分子量: 720.222
• InChiKey: MJDIBWBVPIBBHV-FPGNOWFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  51
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  181
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Ac-(cyclo-m,m)-[(3-Cl)FAAAY]-CO2Me 在 20% palladium hydroxide on charcoal 、 氨 、 氢气 、 lithium hydrochloride monohydrate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 甲醇 、 水 、 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以55%的产率得到Ac-(cyclo-m,m)-[FAAAY]-CO2Me
  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
• 作为产物：
  描述：

  methyl (2S)-3-(3-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 盐酸 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 lithium hydrochloride monohydrate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 cesium fluoride 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 1,4-二氧六环 、 甲醇 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.67h， 生成 Ac-(cyclo-m,m)-[(3-Cl)FAAAY]-CO2Me
  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

文献信息

• Biaryl-Bridged Macrocyclic Peptides: Conformational Constraint via Carbogenic Fusion of Natural Amino Acid Side Chains
  作者：Falco-Magnus Meyer、James C. Collins、Brendan Borin、James Bradow、Spiros Liras、Chris Limberakis、Alan M. Mathiowetz、Laurence Philippe、David Price、Kun Song、Keith James

  DOI：10.1021/jo202105v

  日期：2012.4.6

  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.