tert-butyl ((S)-1-(((2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)amino)-1-oxopropan-2-yl)carbamate | 1186588-78-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: tert-butyl ((S)-1-(((2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)amino)-1-oxopropan-2-yl)carbamate
• CAS: 1186588-78-2
• 化学式: C₃₇H₄₂N₄O₇
• 分子量: 654.763
• InChiKey: DRDPFDIZSSTJBQ-HNEFVXLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  48.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  140.75
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((S)-1-(((2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)amino)-1-oxopropan-2-yl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以59%的产率得到1-(2,3-dideoxy-3-L-alanylamino-β-D-erythro-pentofuranosyl)thymine
  参考文献：
  名称：

  Nucleoside–amino acid conjugates: An alternative route to the design of ribonuclease A inhibitors

  摘要：

  Nucleoside-amino acid conjugates have been employed to inhibit the ribonucleolytic activity of ribonuclease A (RNase A) and affect the protonation/deprotonation equilibrium of its active site histidine residues. Agarose gel and precipitation assays indicate inhibition of RNase A activity by these molecules with a possible role of the polar side chains of the amino acids in RNase A inhibition. Kinetic experiments demonstrated that the mode of inhibition is competitive in nature with inhibition constants (K-i) in the micromolar range. The nucleoside-serine conjugate occupies the active site of RNase A and preferential perturbs the pK(a) value of His-119 by its 'free amino group' as found from H-1 NMR studies. Docking studies revealed that the free amino groups of the most active compounds are within hydrogen bonding distance of His-119 in inhibitor-RNase A complexes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.002
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 、 3'-amino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl ((S)-1-(((2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)amino)-1-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  Nucleoside–amino acid conjugates: An alternative route to the design of ribonuclease A inhibitors

  摘要：

  Nucleoside-amino acid conjugates have been employed to inhibit the ribonucleolytic activity of ribonuclease A (RNase A) and affect the protonation/deprotonation equilibrium of its active site histidine residues. Agarose gel and precipitation assays indicate inhibition of RNase A activity by these molecules with a possible role of the polar side chains of the amino acids in RNase A inhibition. Kinetic experiments demonstrated that the mode of inhibition is competitive in nature with inhibition constants (K-i) in the micromolar range. The nucleoside-serine conjugate occupies the active site of RNase A and preferential perturbs the pK(a) value of His-119 by its 'free amino group' as found from H-1 NMR studies. Docking studies revealed that the free amino groups of the most active compounds are within hydrogen bonding distance of His-119 in inhibitor-RNase A complexes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.002