((S)-1-{(R)-1-Benzyl-3-[(S)-2-((S)-1-tert-butylcarbamoyl-2-methyl-propylcarbamoyl)-pyrrolidin-1-yl]-1-[1,3]dithiolan-2-yl-propylcarbamoyl}-2-methyl-propyl)-carbamic acid benzyl ester | 890022-50-1

• 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: ((S)-1-{(R)-1-Benzyl-3-[(S)-2-((S)-1-tert-butylcarbamoyl-2-methyl-propylcarbamoyl)-pyrrolidin-1-yl]-1-[1,3]dithiolan-2-yl-propylcarbamoyl}-2-methyl-propyl)-carbamic acid benzyl ester
• CAS: 890022-50-1
• 化学式: C₄₀H₅₉N₅O₅S₂
• 分子量: 754.071
• InChiKey: HULOEQXSVDFZPQ-PBLJQIKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  52.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  128.87
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ((S)-1-{(R)-1-Benzyl-3-[(S)-2-((S)-1-tert-butylcarbamoyl-2-methyl-propylcarbamoyl)-pyrrolidin-1-yl]-1-[1,3]dithiolan-2-yl-propylcarbamoyl}-2-methyl-propyl)-carbamic acid benzyl ester 在 三氟化硼乙醚 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以47%的产率得到((S)-1-{(R)-1-Benzyl-3-[(S)-2-((S)-1-tert-butylcarbamoyl-2-methyl-propylcarbamoyl)-pyrrolidin-1-yl]-1-formyl-propylcarbamoyl}-2-methyl-propyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  An unusual functional group interaction and its potential to reproduce steric and electrostatic features of the transition states of peptidolysis

  摘要：

  The donor-acceptor interaction between a tertiary amine and an aldehyde, first observed among a select class of alkaloids, was deliberately established in a peptidomimetic (1a-c) to mimic features of the two principal transition states of peptide hydrolysis. Compounds la-c show preferential adoption in methanol and water of a 'folded' conformation displaying the interaction. Proportions of the folded form in MeOH range from 45% to 70% and can reach 84% in buffer. Significantly, three tendencies for the folded/unfolded equilibrium are observed: increasing solubility and polarity of the medium and decreasing temperature results in a higher extent of folding. In the absence of any parameter set available for this weak bond, no modeling studies were conducted to aid in the design of 1a-c. The successful straightforward synthesis of 1 and its folding and inhibition results with HIV-1 peptidase using FRET technology encourage studies to further preorganize candidate molecules and to screen the structure space by modeling and parallel combinatorial chemistry. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.031
• 作为产物：
  描述：

  {(R)-1-Benzyl-3-[(S)-2-((S)-1-tert-butylcarbamoyl-2-methyl-propylcarbamoyl)-pyrrolidin-1-yl]-1-[1,3]dithiolan-2-yl-propyl}-carbamic acid allyl ester 在 四(三苯基膦)钯 N-羟基-7-氮杂苯并三氮唑 、 5,5-二甲基-1,3-环己二酮 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 ((S)-1-{(R)-1-Benzyl-3-[(S)-2-((S)-1-tert-butylcarbamoyl-2-methyl-propylcarbamoyl)-pyrrolidin-1-yl]-1-[1,3]dithiolan-2-yl-propylcarbamoyl}-2-methyl-propyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  An unusual functional group interaction and its potential to reproduce steric and electrostatic features of the transition states of peptidolysis

  摘要：

  The donor-acceptor interaction between a tertiary amine and an aldehyde, first observed among a select class of alkaloids, was deliberately established in a peptidomimetic (1a-c) to mimic features of the two principal transition states of peptide hydrolysis. Compounds la-c show preferential adoption in methanol and water of a 'folded' conformation displaying the interaction. Proportions of the folded form in MeOH range from 45% to 70% and can reach 84% in buffer. Significantly, three tendencies for the folded/unfolded equilibrium are observed: increasing solubility and polarity of the medium and decreasing temperature results in a higher extent of folding. In the absence of any parameter set available for this weak bond, no modeling studies were conducted to aid in the design of 1a-c. The successful straightforward synthesis of 1 and its folding and inhibition results with HIV-1 peptidase using FRET technology encourage studies to further preorganize candidate molecules and to screen the structure space by modeling and parallel combinatorial chemistry. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.031