tert-butyl (2R,3S)-3-hydroxy-4-[(S)-4-methyl-1-(methylamino)-1-oxopentan-2-ylamino]-4-oxo-1-phenylbutan-2-ylcarbamate | 1312302-10-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: tert-butyl (2R,3S)-3-hydroxy-4-[(S)-4-methyl-1-(methylamino)-1-oxopentan-2-ylamino]-4-oxo-1-phenylbutan-2-ylcarbamate
• CAS: 1312302-10-5
• 化学式: C₂₂H₃₅N₃O₅
• 分子量: 421.537
• InChiKey: OSLIAHPAOZOJEF-SQNIBIBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  116.76
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,3S)-3-hydroxy-4-[(S)-4-methyl-1-(methylamino)-1-oxopentan-2-ylamino]-4-oxo-1-phenylbutan-2-ylcarbamate 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到(S)-2-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido]-N,4-dimethylpentanamide hydrochloride
  参考文献：
  名称：

  Development of target protein-selective degradation inducer for protein knockdown

  摘要：

  Our previous technique for inducing selective degradation of target proteins with ester-type SNIPER (Specific and Nongenetic Inhibitor-of-apoptosis-proteins (IAPs)-dependent Protein ERaser) degrades both the target proteins and IAPs. Here, we designed a small-molecular amide-type SNIPER to overcome this issue. As proof of concept, we synthesized and biologically evaluated an amide-type SNIPER which induces selective degradation of cellular retinoic acid binding protein II (CRABP-II), but not IAPs. Such small-molecular, amide-type SNIPERs that induce target protein-selective degradation without affecting IAPs should be effective tools to study the biological roles of target proteins in living cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.057
• 作为产物：
  描述：

  乌苯美司 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 46.0h， 生成 tert-butyl (2R,3S)-3-hydroxy-4-[(S)-4-methyl-1-(methylamino)-1-oxopentan-2-ylamino]-4-oxo-1-phenylbutan-2-ylcarbamate
  参考文献：
  名称：

  Development of target protein-selective degradation inducer for protein knockdown

  摘要：

  Our previous technique for inducing selective degradation of target proteins with ester-type SNIPER (Specific and Nongenetic Inhibitor-of-apoptosis-proteins (IAPs)-dependent Protein ERaser) degrades both the target proteins and IAPs. Here, we designed a small-molecular amide-type SNIPER to overcome this issue. As proof of concept, we synthesized and biologically evaluated an amide-type SNIPER which induces selective degradation of cellular retinoic acid binding protein II (CRABP-II), but not IAPs. Such small-molecular, amide-type SNIPERs that induce target protein-selective degradation without affecting IAPs should be effective tools to study the biological roles of target proteins in living cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.057