Fmoc-Leu-Lys(Boc)-Leu-His(Trt)-Leu-NH2 | 760978-09-4

• 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: Fmoc-Leu-Lys(Boc)-Leu-His(Trt)-Leu-NH2
• CAS: 760978-09-4
• 化学式: C₆₉H₈₇N₉O₉
• 分子量: 1186.5
• InChiKey: KIXXEIRKGILOLO-HAUDDGJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.43
• 重原子数：
  87.0
• 可旋转键数：
  29.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  253.97
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Leu-Lys(Boc)-Leu-His(Trt)-Leu-NH2 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以91%的产率得到H-Leu-Lys(Boc)-Leu-His(Trt)-Leu-NH2
  参考文献：
  名称：

  Thermodynamic and Kinetic Stability of Synthetic Multifunctional Rigid-Rod β-Barrel Pores:  Evidence for Supramolecular Catalysis

  摘要：

  The lessons learned from p-octiphenyl beta-barrel pores are applied to the rational design of synthetic multifunctional pore 1 that is unstable but inert, two characteristics proposed to be ideal for practical applications. Nonlinear dependence on monomer concentration provided direct evidence that pore 1 is tetrameric (n = 4.0), unstable, and "invisible," i.e., incompatible with structural studies by conventional methods. The long lifetime of high-conductance single pores in planar bilayers demonstrated that rigid-rod beta-barrel 1 is inert and large (d approximate to 12 Angstrom). Multifunctionality of rigid-rod beta-barrel 1 was confirmed by adaptable blockage of pore host 1 with representative guests in planar (8-hydroxy-1,3,6-pyrenetrisulfonate, K-D = 190 muM, n = 4.9) and spherical bilayers (poly-L-glutamate, K-D less than or equal to 105 nM, n = 1.0; adenosine triphosphate, K-D = 240 muM, n = 2.0) and saturation kinetics for the esterolysis of a representative substrate (8-acetoxy-1,3,6-pyrenetrisulfonate, K-M = 0.6 muM). The thermodynamic instability of rigid-rod beta-barrel 1 provided unprecedented access to experimental evidence for supramolecular catalysis (n = 3.7). Comparison of the obtained k(cat) = 0.03 min(-1) with the k(cat) approximate to 0.18 min(-1) for stable analogues gave a global K-D approximate to 39 muM(3) for supramolecular catalyst 1 with a monomer/barrel ratio approximate to 20 under experimental conditions. The demonstrated "invisibility" of supramolecular multifunctionality identified molecular modeling as an attractive method to secure otherwise elusive insights into structure. The first molecular mechanics modeling (MacroModel, MMFF94) of multifunctional rigid-rod beta-barrel pore hosts 1 with internal 1,3,6-pyrenetrisulfonate guests is reported.

  DOI：

  10.1021/ja0481878
• 作为产物：
  描述：

  Fmoc-Lys(Boc)-Leu-His(Trt)-Leu-NH2 在 哌啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 Fmoc-Leu-Lys(Boc)-Leu-His(Trt)-Leu-NH2
  参考文献：
  名称：

  Thermodynamic and Kinetic Stability of Synthetic Multifunctional Rigid-Rod β-Barrel Pores:  Evidence for Supramolecular Catalysis

  摘要：

  The lessons learned from p-octiphenyl beta-barrel pores are applied to the rational design of synthetic multifunctional pore 1 that is unstable but inert, two characteristics proposed to be ideal for practical applications. Nonlinear dependence on monomer concentration provided direct evidence that pore 1 is tetrameric (n = 4.0), unstable, and "invisible," i.e., incompatible with structural studies by conventional methods. The long lifetime of high-conductance single pores in planar bilayers demonstrated that rigid-rod beta-barrel 1 is inert and large (d approximate to 12 Angstrom). Multifunctionality of rigid-rod beta-barrel 1 was confirmed by adaptable blockage of pore host 1 with representative guests in planar (8-hydroxy-1,3,6-pyrenetrisulfonate, K-D = 190 muM, n = 4.9) and spherical bilayers (poly-L-glutamate, K-D less than or equal to 105 nM, n = 1.0; adenosine triphosphate, K-D = 240 muM, n = 2.0) and saturation kinetics for the esterolysis of a representative substrate (8-acetoxy-1,3,6-pyrenetrisulfonate, K-M = 0.6 muM). The thermodynamic instability of rigid-rod beta-barrel 1 provided unprecedented access to experimental evidence for supramolecular catalysis (n = 3.7). Comparison of the obtained k(cat) = 0.03 min(-1) with the k(cat) approximate to 0.18 min(-1) for stable analogues gave a global K-D approximate to 39 muM(3) for supramolecular catalyst 1 with a monomer/barrel ratio approximate to 20 under experimental conditions. The demonstrated "invisibility" of supramolecular multifunctionality identified molecular modeling as an attractive method to secure otherwise elusive insights into structure. The first molecular mechanics modeling (MacroModel, MMFF94) of multifunctional rigid-rod beta-barrel pore hosts 1 with internal 1,3,6-pyrenetrisulfonate guests is reported.

  DOI：

  10.1021/ja0481878