[5-(2)H]-2',3'-O-isopropylidene-5'-deoxy-5'-uridylaldehyde | 1360455-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: [5-(2)H]-2',3'-O-isopropylidene-5'-deoxy-5'-uridylaldehyde
• CAS: 1360455-14-6
• 化学式: C₁₂H₁₄N₂O₆
• 分子量: 283.245
• InChiKey: ULFDPCIPYCEREB-AAMXCVFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.85
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  99.62
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2',3'-O-Isopropyliden-(5-D)uridin 在 2-碘酰基苯甲酸 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 [5-(2)H]-2',3'-O-isopropylidene-5'-deoxy-5'-uridylaldehyde
  参考文献：
  名称：

  Biogenesis of the Unique 4′,5′-Dehydronucleoside of the Uridyl Peptide Antibiotic Pacidamycin

  摘要：

  The pacidamycins belong to a class of antimicrobial nucleoside antibiotics that act by inhibiting the clinically unexploited target translocase I, a key enzyme in peptidoglycan assembly. As with other nucleoside antibiotics, the pacidamycin 4',5'-dehydronucleoside portion is an essential pharmacophore. Here we show that the biosynthesis of the pacidamycin nucleoside in Streptomyces coeruleorubidus proceeds through three steps from uridine. The transformations involve oxidation of the 5'-alcohol by Pac11, transamination of the resulting aldehyde by Pac5, and dehydration by the Cupin-domain protein Pac13.

  DOI：

  10.1021/ja206163j