4-Oxo-pentanoic acid (2R,3S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-{(2-cyano-ethoxy)-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester | 215116-98-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 4-Oxo-pentanoic acid (2R,3S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-{(2-cyano-ethoxy)-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-[[2-cyanoethoxy-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphoryl]oxymethyl]oxolan-3-yl] 4-oxopentanoate
• CAS: 215116-98-6
• 化学式: C₂₇H₃₅N₆O₁₃P
• 分子量: 682.581
• InChiKey: BVKHQRDHVFNKHY-PVJIQYRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  259
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  4-Oxo-pentanoic acid (2R,3S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-{(2-cyano-ethoxy)-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester 在 一水合肼 作用下， 以 水 为溶剂， 生成 5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)-T(6-4)C 3'-(2-cyanoethyl)-N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Chemical Synthesis of Oligonucleotides Containing The (6-4) Photoproduct at the Thymine-Cytosine Site and Its Repair By (6-4) Photolyase

  摘要：

  A phosphoramidite building block of the T(6-4)C photoproduct was synthesized. One of the differences from T(6-4)T was formation of cytosine hydrates by UV irradiation, and the other was acylation of the amino function with the capping reagent. The capping step was omitted to improve the yield of the desired oligonucleotides. Characterization of the (6-4) photolyase using one of the oligonucleotides revealed that this enzyme restores the pyrimidines in T(6-4)C to their original structures.

  DOI：

  10.1080/07328319908044706
• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 在 四氮唑 、 碘 、 N,N'-二环己基碳二亚胺 、 zinc dibromide 、 三氯乙酸 作用下， 以 水 为溶剂， 生成 4-Oxo-pentanoic acid (2R,3S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-{(2-cyano-ethoxy)-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Chemical Synthesis of Oligonucleotides Containing The (6-4) Photoproduct at the Thymine-Cytosine Site and Its Repair By (6-4) Photolyase

  摘要：

  A phosphoramidite building block of the T(6-4)C photoproduct was synthesized. One of the differences from T(6-4)T was formation of cytosine hydrates by UV irradiation, and the other was acylation of the amino function with the capping reagent. The capping step was omitted to improve the yield of the desired oligonucleotides. Characterization of the (6-4) photolyase using one of the oligonucleotides revealed that this enzyme restores the pyrimidines in T(6-4)C to their original structures.

  DOI：

  10.1080/07328319908044706

文献信息

• Studies on the Chemical Synthesis of Oligonucleotides Containing the (6−4) Photoproduct of Thymine−Cytosine and Its Repair by (6−4) Photolyase
  作者：Toshimi Mizukoshi、Kenichi Hitomi、Takeshi Todo、Shigenori Iwai

  DOI：10.1021/ja982004y

  日期：1998.10.1

  To prepare oligonucleotides containing the pyrimidine(6-4)pyrimidone photoproduct between thymine and cytosine, which is formed more efficiently than any counterpart at other dipyrimidine sites, a dimer building block of this photoproduct was synthesized. Irradiation of thymidylyl(3'-5')deoxycytidine, with protecting groups at the phosphate and the 3'-hydroxyl function, gave a hydrate of cytosine as the main product, and the formation of the (6-4) photoproduct reached a plateau faster than that from the thymidylyl(3'-5')thymidine derivative. After chromatographic purification of the desired (6-4) photoproduct, a phosphoramidite building block was synthesized in three steps. When this compound was used for the usual oligonucleotide assembly on a solid support, it was found that acylation of the amino group of the 5'-pyrimidine component occurred at the capping step. Oligonucleotides were synthesized successfully by omitting the capping steps after coupling of the (6-4) photoproduct unit. These synthetic oligonucleotides were applied to the characterization of the (6-4) photolyase. By HPLC analyses of the photoreactivation product and its nucleoside composition, it was demonstrated that this (6-4) photoproduct was repaired to its original pyrimidine components by this enzyme.