(3S)-3-amino-N-[(2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydrofuran-3-yl]-succinamic acid | 1261085-21-5

• 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: (3S)-3-amino-N-[(2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydrofuran-3-yl]-succinamic acid
• CAS: 1261085-21-5
• 化学式: C₁₄H₂₀N₄O₇
• 分子量: 356.335
• InChiKey: LJTMXEFTZIGLGL-AXTSPUMRSA-N

反应信息

• 作为产物：
  描述：

  (3S)-3-tert-butoxycarbonylamino-N-[(2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydrofuran-3-yl]-succinamic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以0.06 g的产率得到(3S)-3-amino-N-[(2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydrofuran-3-yl]-succinamic acid
  参考文献：
  名称：

  Comparative inhibitory activity of 3′- and 5′-functionalized nucleosides on ribonuclease A

  摘要：

  Modified nucleosides, molecules, functionalized with various polar groups at different positions have been synthesized to rationalize the impact of structural modification on their inhibitory activity. Agarose gel and precipitation assays indicate their improved inhibitory activity on ribonuclease A (RNase A). Kinetic experiments clearly categorize them as competitive inhibitors of RNase A with improved inhibition constant (K-i) values (37 +/- 9, 67 +/- 6, and 193 +/- 7 mu M for compounds 10, 3, and 7, respectively). The preferential hydrogen bonding network formation between His-12 and His-119 of RNase A with the polar carboxylic and amino groups of these compounds has been evidenced from the docking studies. The relationship between structural modifications and inhibitory activity of these compounds is further justified in terms of energetics using PEARLS. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.005