[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-(3-methylimidazol-3-ium-1-yl)phosphinate | 109708-45-4

• 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: [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-(3-methylimidazol-3-ium-1-yl)phosphinate
• CAS: 109708-45-4
• 化学式: C₁₄H₁₉N₄O₇P
• 分子量: 386.301
• InChiKey: XSWZUJPRJDEULL-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.85
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  142.49
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  γ-aminobutyrylhistamine 、 [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-(3-methylimidazol-3-ium-1-yl)phosphinate 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以43%的产率得到2'-deoxythymidine-5'-N-(3-{N-[2-(1H-imidazol-4-yl)ethyl]carbamoyl}propyl)phosphamide lithium salt
  参考文献：
  名称：

  摘要：

  The reactions of histamine, the natural dipeptide carcinine (beta-Ala-HA), and its analogs with 5'-monodeoxyribonucleotides (dNMP) in the presence of triphenylphosphine, 2,2'-dipyridyl disulfide, and N-methylimidazole were studied. The yield of phosphamide derivatives decreases from 72% to 17% as the length of the linker group between the imidazole ring and the terminal aliphatic amino group is increased. Hydrolytic stability of the resulting conjugates was examined. The stability of the bonds in the -O-P(O)(2)-NH- group linking the nucleotide and peptide portions of the conjugate depends on the nature of the heterocyclic base of the nucleotide and decreases in the series dTMP > dCMP > dAMP.

  DOI：

  10.1023/a:1021329324527
• 作为产物：
  描述：

  N-甲基咪唑 、 TMP triethylammonium salt 在 2,2'-二硫二吡啶 、 三苯基膦 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-(3-methylimidazol-3-ium-1-yl)phosphinate
  参考文献：
  名称：

  摘要：

  The reactions of histamine, the natural dipeptide carcinine (beta-Ala-HA), and its analogs with 5'-monodeoxyribonucleotides (dNMP) in the presence of triphenylphosphine, 2,2'-dipyridyl disulfide, and N-methylimidazole were studied. The yield of phosphamide derivatives decreases from 72% to 17% as the length of the linker group between the imidazole ring and the terminal aliphatic amino group is increased. Hydrolytic stability of the resulting conjugates was examined. The stability of the bonds in the -O-P(O)(2)-NH- group linking the nucleotide and peptide portions of the conjugate depends on the nature of the heterocyclic base of the nucleotide and decreases in the series dTMP > dCMP > dAMP.

  DOI：

  10.1023/a:1021329324527