S-geranyl-2-thiouridine | 1401688-09-2

• 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: S-geranyl-2-thiouridine
• 英文别名: 2-Geranylthiouridine；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-[(2E)-3,7-dimethylocta-2,6-dienyl]sulfanylpyrimidin-4-one
• CAS: 1401688-09-2
• 化学式: C₁₉H₂₈N₂O₅S
• 分子量: 396.508
• InChiKey: KFZLIRUEFHTLEW-ZGFVZBPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-geranyl-2-thiouridine 在 吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 5'-O-dimetoxytrityl-2-selenouridine
  参考文献：
  名称：

  Transformation of a wobble 2-thiouridine to 2-selenouridine via S-geranyl-2-thiouridine as a possible cellular pathway

  摘要：

  The newly discovered S-geranylated 2-thiouridines (geS2U) (Dumelin et al., 2012) and 2-selenouridines (Se2U) were recently shown to be synthesized by a single enzyme (selenouridine synthase, SelU) through two distinct pathways using the same 2-thiouridine substrate (S2U); however, no clear catalytic mechanism was proposed. We suggest that S-geranyl-2-thiouridine is an intermediate of the SelU-catalyzed conversion of S2U to Se2U. The successful chemical transformation of S2U -> geS2U -> Se2U is demonstrated here as an initial approximation of the intracellular pathway. The structure of Se2U was confirmed by spectroscopic methods, which included, for the first time, Se-77 NMR data (delta 354 ppm). (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.05.012
• 作为产物：
  描述：

  香叶基溴 、 2-硫代尿苷 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以89%的产率得到S-geranyl-2-thiouridine
  参考文献：
  名称：

  Transformation of a wobble 2-thiouridine to 2-selenouridine via S-geranyl-2-thiouridine as a possible cellular pathway

  摘要：

  The newly discovered S-geranylated 2-thiouridines (geS2U) (Dumelin et al., 2012) and 2-selenouridines (Se2U) were recently shown to be synthesized by a single enzyme (selenouridine synthase, SelU) through two distinct pathways using the same 2-thiouridine substrate (S2U); however, no clear catalytic mechanism was proposed. We suggest that S-geranyl-2-thiouridine is an intermediate of the SelU-catalyzed conversion of S2U to Se2U. The successful chemical transformation of S2U -> geS2U -> Se2U is demonstrated here as an initial approximation of the intracellular pathway. The structure of Se2U was confirmed by spectroscopic methods, which included, for the first time, Se-77 NMR data (delta 354 ppm). (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.05.012