3',5'-di-O-Lev-β-D-U | 461426-84-6

• 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: 3',5'-di-O-Lev-β-D-U
• CAS: 461426-84-6
• 化学式: C₁₉H₂₄N₂O₁₀
• 分子量: 440.407
• InChiKey: VIZXNAFHVDQSKJ-BDQAWRDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.01
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  171.06
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  尿嘧啶核苷 、 acetonoxime levulinate 在 Pseudomonas cepacia lipase 、 Candida antarctica lipase B 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 2',5'-di-O-Lev-β-D-U 、 5'-O-levulinoyl-β-L-uridine 、 5'-O-levulinyl ribouridine 、 3',5'-di-O-Lev-β-D-U
  参考文献：
  名称：

  Enzymatic Parallel Kinetic Resolution of Mixtures of d/l 2′-Deoxy and Ribonucleosides: An Approach for the Isolation of β-l-Nucleosides

  摘要：

  We have developed a lipase-catalyzed parallel kinetic resolution of mixtures of beta-D/L-nucleosides. The opposite selectivity during acylation exhibited by Pseudomonas cepacia lipase (PSL-C) with beta-D- and beta-L-nucleosides furnished acylated compounds that have different R-f values. As a consequence, isolation of both products was achieved by simple column chromatography. Computer modeling of the transition-state analogues during acylation of beta-D- and beta-L-2'-deoxycytidine with PSL-C was carried out to explain the high selectivity. PSL-C favored the 3'-O-levulination of the beta-D enantiomer, whereas the 5'-OH group was acylated in 2'-deoxy-beta-L-cytidine. In both cases, the cytosine base was placed in the alternate hydrophobic pocket of PSL's substrate-binding site, where it can form extra hydrogen bonds (in addition to the five essential catalytically relevant hydrogen bonds) that stabilize these intermediates catalyzing the selective acylation of beta-D/L-nucleosides.

  DOI：

  10.1021/jo101368z