N1,N6-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide | 361433-05-8

• 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: N1,N6-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide
• CAS: 361433-05-8
• 化学式: C₄₁H₆₁BrN₆O₁₁
• 分子量: 893.873
• InChiKey: ROOXDGPWIDKESV-WLVAUIPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.54
• 重原子数：
  59.0
• 可旋转键数：
  27.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  248.9
• 氢给体数：
  8.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  succinimidyl-6-(biotinamido)hexanoate 、 N1,N6-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以96%的产率得到N1,N6-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-[4-((E)-2-{N-[2-(2-{2-[6-(biotiamido)carbamoylpentyl]ethoxy}ethoxy)ethyl]}carbamoylethenyl)benzyloxy]-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide
  参考文献：
  名称：

  P1/P1′ modified HIV protease inhibitors as tools in two new sensitive surface plasmon resonance biosensor screening assays

  摘要：

  The commonly used HIV-1 protease assays rely on measurements of the effect of inhibitions on the hydrolysis rate of synthetic peptides. Recently an assay based on surface plasmon resonance (SPR) was introduced. We have taken advantage of the fact that the SPR signal is proportional to the mass of the analyte interacting with the immobilised molecule and developed two new improved efficient competition assay methods. Thus. high molecular weight binders were used as amplifiers of the surface plasmon resonance signal. Linkers were attached by a Heck reaction to the para-positions of the P1/P1' benzyloxy groups of a linear C-2-symmetric C-terminal duplicated inhibitor to enable (a) biotin labelling or (b) direct immobilisation of the inhibitor to the biosensor surface matrix. The interaction properties of a series of 17 structurally diverse inhibitors was assessed and compared to previously reported data. The most sensitive assay was obtained by immobilising the enzyme and amplifying the signal with an antibody, giving a detection range between 0.1 nM and 10 muM Immobilisation of the inhibitor resulted in a stable and durable surface but a narrower detection range (1-100 nM). The two competition assays are anticipated to be very suitable for fast screening of potential HIV inhibitors. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(01)00109-9
• 作为产物：
  描述：

  2-(2-(2-氨基乙氧基)乙氧基)乙基氨基甲酸叔丁酯 在 palladium diacetate N,N-二异丙基乙胺 、 三(邻甲基苯基)磷 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.17h， 生成 N1,N6-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide
  参考文献：
  名称：

  P1/P1′ modified HIV protease inhibitors as tools in two new sensitive surface plasmon resonance biosensor screening assays

  摘要：

  The commonly used HIV-1 protease assays rely on measurements of the effect of inhibitions on the hydrolysis rate of synthetic peptides. Recently an assay based on surface plasmon resonance (SPR) was introduced. We have taken advantage of the fact that the SPR signal is proportional to the mass of the analyte interacting with the immobilised molecule and developed two new improved efficient competition assay methods. Thus. high molecular weight binders were used as amplifiers of the surface plasmon resonance signal. Linkers were attached by a Heck reaction to the para-positions of the P1/P1' benzyloxy groups of a linear C-2-symmetric C-terminal duplicated inhibitor to enable (a) biotin labelling or (b) direct immobilisation of the inhibitor to the biosensor surface matrix. The interaction properties of a series of 17 structurally diverse inhibitors was assessed and compared to previously reported data. The most sensitive assay was obtained by immobilising the enzyme and amplifying the signal with an antibody, giving a detection range between 0.1 nM and 10 muM Immobilisation of the inhibitor resulted in a stable and durable surface but a narrower detection range (1-100 nM). The two competition assays are anticipated to be very suitable for fast screening of potential HIV inhibitors. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(01)00109-9