phenacyl 4-<<α-(tert-butoxycarbonyl)-N^ε-(9-fluorenylmethoxycarbonyl)-L-lysyl-L-prolyl>oxy>methyl>benzoate | 136631-88-4

• 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: phenacyl 4-<<α-(tert-butoxycarbonyl)-N^ε-(9-fluorenylmethoxycarbonyl)-L-lysyl-L-prolyl>oxy>methyl>benzoate
• 英文别名: phenacyl 4-({[N^α-(tert-butoxycarbonyl)-N^ε-(9-fluorenylmethoxycarbonyl)-L-lysyl-L-prolyl]oxy}methyl)benzoate；(4-phenacyloxycarbonylphenyl)methyl (2S)-1-[(2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]pyrrolidine-2-carboxylate
• CAS: 136631-88-4
• 化学式: C₄₇H₅₁N₃O₁₀
• 分子量: 817.936
• InChiKey: VCJUUMKKHYSKLH-ZAQUEYBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.36
• 重原子数：
  60.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  166.64
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  phenacyl 4-<<α-(tert-butoxycarbonyl)-N^ε-(9-fluorenylmethoxycarbonyl)-L-lysyl-L-prolyl>oxy>methyl>benzoate 在 水 、 溶剂黄146 、 锌 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以89%的产率得到4-<<α-(tert-butoxycarbonyl)-N^ε-(9-fluorenylmethoxycarbonyl)-L-lysyl-L-prolyl>oxy>methyl>benzoic acid
  参考文献：
  名称：

  Direct cleavage of peptides from a solid support into aqueous buffer. Application in simultaneous multiple peptide synthesis

  摘要：

  A method of simultaneous multiple peptide synthesis which integrates synthesis, side-chain deprotection, cleavage, and purification so as to afford peptide solutions suitable for immediate biological testing is described. The approach utilizes a novel diketopiperazine-forming cleavable linker 1. Upon side-chain deprotection, 1 gives 2, which is stable to a protocol designed to remove contaminants from the support-bound peptide prior to cleavage. Peptide cleavage is then effected by treating 2 with a neutral or near neutral buffer to give peptide 4, which carries a C-terminal diketopiperazine moiety, in good yield. In this study the glycolamido and 4-(oxymethyl)benzamido esters of 1 have been appraised. The approach is demonstrated in model studies on 7 and 8 and in the preparation and characterization of peptides 17-21. The general approach allows 10-100-nmol quantities of many hundreds of peptides to be concurrently prepared in a relatively short period of time when used in conjunction with the multipin method of multiple peptide synthesis.

  DOI：

  10.1021/jo00023a035
• 作为产物：
  描述：

  BOC-L-脯氨酸 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 phenacyl 4-<<α-(tert-butoxycarbonyl)-N^ε-(9-fluorenylmethoxycarbonyl)-L-lysyl-L-prolyl>oxy>methyl>benzoate
  参考文献：
  名称：

  Direct cleavage of peptides from a solid support into aqueous buffer. Application in simultaneous multiple peptide synthesis

  摘要：

  A method of simultaneous multiple peptide synthesis which integrates synthesis, side-chain deprotection, cleavage, and purification so as to afford peptide solutions suitable for immediate biological testing is described. The approach utilizes a novel diketopiperazine-forming cleavable linker 1. Upon side-chain deprotection, 1 gives 2, which is stable to a protocol designed to remove contaminants from the support-bound peptide prior to cleavage. Peptide cleavage is then effected by treating 2 with a neutral or near neutral buffer to give peptide 4, which carries a C-terminal diketopiperazine moiety, in good yield. In this study the glycolamido and 4-(oxymethyl)benzamido esters of 1 have been appraised. The approach is demonstrated in model studies on 7 and 8 and in the preparation and characterization of peptides 17-21. The general approach allows 10-100-nmol quantities of many hundreds of peptides to be concurrently prepared in a relatively short period of time when used in conjunction with the multipin method of multiple peptide synthesis.

  DOI：

  10.1021/jo00023a035