2-[2-((S)-2,6-Diamino-hexanoylamino)-acetylamino]-3-phenyl-propionic acid 3-[({[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-methyl}-amino)-methyl]-2-mercapto-phenyl ester | 901126-83-8

• 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: 2-[2-((S)-2,6-Diamino-hexanoylamino)-acetylamino]-3-phenyl-propionic acid 3-[({[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-methyl}-amino)-methyl]-2-mercapto-phenyl ester
• CAS: 901126-83-8
• 化学式: C₄₄H₅₄N₈O₇S
• 分子量: 839.028
• InChiKey: YLXHJBZUCVKHFW-SFGGGBLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  60.0
• 可旋转键数：
  24.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  249.86
• 氢给体数：
  9.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-[2-((S)-2,6-Diamino-hexanoylamino)-acetylamino]-3-phenyl-propionic acid 3-[({[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-methyl}-amino)-methyl]-2-mercapto-phenyl ester 以 甲醇 为溶剂， 反应 1.0h， 生成 (S)-2,6-Diamino-hexanoic acid ({1-[{[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-methyl}-(3-hydroxy-2-mercapto-benzyl)-carbamoyl]-2-phenyl-ethylcarbamoyl}-methyl)-amide 、
  参考文献：
  名称：

  Studies Related to the Relative Thermodynamic Stability of C-Terminal Peptidyl Esters of O-Hydroxy Thiophenol:  Emergence of a Doable Strategy for Non-Cysteine Ligation Applicable to the Chemical Synthesis of Glycopeptides

  摘要：

  A pathway has been devised, wherein a phenolic ester of a C-terminal peptide is ligated with an N-terminal peptide through two consecutive acyl migrations. In the first transacylation, the C-terminus is transferred from a phenol to a newly liberated ortho-thiol function. Subsequently, the acyl group is transported to a proximal benzylamine through a six-membered transition state.

  DOI：

  10.1021/ja061588y
• 作为产物：
  描述：

  2-hydroxy-3-((2-methoxyethoxy)methoxy)benzaldehyde 在 氢氧化钾 、 sodium hydroxide 、 N-氯代丁二酰亚胺 、 三异丙基硅烷 、 sodium cyanoborohydride 、 1-羟基苯并三唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 三甘醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.92h， 生成 2-[2-((S)-2,6-Diamino-hexanoylamino)-acetylamino]-3-phenyl-propionic acid 3-[({[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-methyl}-amino)-methyl]-2-mercapto-phenyl ester
  参考文献：
  名称：

  Studies Related to the Relative Thermodynamic Stability of C-Terminal Peptidyl Esters of O-Hydroxy Thiophenol:  Emergence of a Doable Strategy for Non-Cysteine Ligation Applicable to the Chemical Synthesis of Glycopeptides

  摘要：

  A pathway has been devised, wherein a phenolic ester of a C-terminal peptide is ligated with an N-terminal peptide through two consecutive acyl migrations. In the first transacylation, the C-terminus is transferred from a phenol to a newly liberated ortho-thiol function. Subsequently, the acyl group is transported to a proximal benzylamine through a six-membered transition state.

  DOI：

  10.1021/ja061588y