2',3'-dideoxy-3'-L-valinylamino-thymidine | 1186588-68-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2',3'-dideoxy-3'-L-valinylamino-thymidine
• 英文别名: Val-aT；(2S)-2-amino-N-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-3-methylbutanamide
• CAS: 1186588-68-0
• 化学式: C₁₅H₂₄N₄O₅
• 分子量: 340.379
• InChiKey: PRFIOGFTNOKBOR-QCNOEVLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  benzyl N-[(2S)-1-[[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate 生成 2',3'-dideoxy-3'-L-valinylamino-thymidine
  参考文献：
  名称：

  MORINIERE, JEAN-LUC;FAUIQUES, MICHELLE;ROUSSEAU, CLAUDE;DANREE, BERNARD;M+

  摘要：

  DOI：

文献信息

• Nucleoside–amino acid conjugates: An alternative route to the design of ribonuclease A inhibitors
  作者：Joy Debnath、Swagata Dasgupta、Tanmaya Pathak

  DOI：10.1016/j.bmc.2009.06.002

  日期：2009.7

  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.
• US5212161A
  申请人：——

  公开号：US5212161A

  公开（公告）日：1993-05-18