5'-O-β-D-galactosyl-5-bromo-2'-deoxyuridine | 1385778-50-6

• 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: 5'-O-β-D-galactosyl-5-bromo-2'-deoxyuridine
• CAS: 1385778-50-6
• 化学式: C₁₅H₂₁BrN₂O₁₀
• 分子量: 469.243
• InChiKey: WAXPHLBWKDDLFW-MHHJMVSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.24
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  183.7
• 氢给体数：
  6.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  溴脲苷 、 尾-D-Galactoside,2-nitrophenyl(9CI) 在 β-galactosidase 作用下， 反应 65.0h， 以38%的产率得到5'-O-β-D-galactosyl-5-bromo-2'-deoxyuridine
  参考文献：
  名称：

  Facile and regioselective enzymatic 5′-galactosylation of pyrimidine 2′-deoxynucleosides catalyzed by β-glycosidase from bovine liver

  摘要：

  A regioselective enzymatic approach to 5'-O-galactosylated derivatives of pyrimidine 2'-deoxynucleosides was described. With o-nitrophenyl beta-D-galactoside as glycosyl donor, galactosylation reactions of 2'-deoxynucleosides were mediated by a commercial beta-galactosidase from bovine liver, affording 5'-O-galactosylated derivatives with the yields of 45-85% and 5'-regioselectivities of 92-100%. The study of enzyme substrate recognition revealed that the beta-galactosidase performance showed a clear dependence on R-group present in the base moiety of 2'-deoxynucleoside. Besides, such desirable products were synthesized with satisfactory yields (41-68%) and moderate to high 5'-regioselectivities (87-100%) by using the crude enzyme extract. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.03.018