Phosphoric acid (2R,3S,4R,5R)-4-carbamoylmethyl-2-hydroxymethyl-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 英文名称: Phosphoric acid (2R,3S,4R,5R)-4-carbamoylmethyl-2-hydroxymethyl-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• 英文别名: [(2R,3S,4R,5R)-4-(2-amino-2-oxoethyl)-5-(2,4-dioxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] [(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
• 化学式: C₂₀H₂₆N₅O₁₄P
• 分子量: 591.425
• InChiKey: XGTIUZONDAHQJH-FCYBQJKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.1
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  277
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Phosphoric acid (2R,3S,4R,5R)-4-carbamoylmethyl-2-hydroxymethyl-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 在 sodium hydroxide 作用下， 反应 96.0h， 生成 2-[(2R,3R,4S,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(hydroxymethyl)oxolan-3-yl]acetic acid
  参考文献：
  名称：

  The Synthesis of 2′-C-Functionalised Nucleosides for Incorporation into Catalytic RNA

  摘要：

  Five 2'-C-functionalized nucleosides (1-5) have been prepared and incorporated into dinucleoside monophosphates. The effect of the functionality on the stability of the adjacent phosphodiester bond toward hydrolysis by nuclease enzymes and extremes of pH has been assessed.

  DOI：

  10.1080/07328319708006215
• 作为产物：
  描述：

  benzhydryl 2-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxy-2-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl]acetate 在 甲醇 、 氨 、 溶剂黄146 作用下， 反应 2.0h， 生成 Phosphoric acid (2R,3S,4R,5R)-4-carbamoylmethyl-2-hydroxymethyl-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Synthesis and Properties of 2‘-Deoxy-2‘-α-C-branched Nucleosides and Nucleotides

  摘要：

  Four functionalized 2'-deoxy-2'-alpha-C-branched nucleosides, namely, 2'-deoxy-2'-alpha-C-(carboxymethyl)-uridine, 2'-deoxy-2'-alpha-acetamidouridine, 2'-deoxy-2'-alpha-C-(hydroxyethyl)uridine, and 2'-deoxy-2'-alpha-C-(2,3-dihydroxypropyl)uridine, have been prepared. Conversion of these nucleosides to their appropriately protected phosphoramidites, followed by tetrazole-induced reaction with 2',3'-di-O-acetyluridine, oxidation, and subsequent deprotection furnished the corresponding dinucleoside monophosphates. During the oxidation of the amide-derived phosphite, partial dehydration occurred to give a mixture of the amide- and nitrile-containing dimers. Interestingly, the ratio of amide to nitrile could be largely controlled by choice of oxidant. The hydroxyethyl- and dihydroxypropyl-modified dimers were particularly resistant to snake venom phosphodiesterase-catalyzed hydrolysis (relative half-lives of 129 and 120, respectively, in comparison to UpU). It is anticipated that these nucleoside analogues will ultimately be used in the construction of ribozymes containing enhanced functionality and nuclease resistance.

  DOI：

  10.1021/jo9614607

文献信息

• The Synthesis of 2′-C-Functionalised Nucleosides for Incorporation into Catalytic RNA
  作者：Anthony J. Lawrence、John B. J. Pavey、Ian A. O'Neil、Richard Cosstick

  DOI：10.1080/07328319708006215

  日期：1997.7

  Five 2'-C-functionalized nucleosides (1-5) have been prepared and incorporated into dinucleoside monophosphates. The effect of the functionality on the stability of the adjacent phosphodiester bond toward hydrolysis by nuclease enzymes and extremes of pH has been assessed.
• Synthesis and Properties of 2‘-Deoxy-2‘-α-<i>C</i>-branched Nucleosides and Nucleotides
  作者：Anthony J. Lawrence、John B. J. Pavey、Richard Cosstick、Ian A. O'Neil

  DOI：10.1021/jo9614607

  日期：1996.1.1

  Four functionalized 2'-deoxy-2'-alpha-C-branched nucleosides, namely, 2'-deoxy-2'-alpha-C-(carboxymethyl)-uridine, 2'-deoxy-2'-alpha-acetamidouridine, 2'-deoxy-2'-alpha-C-(hydroxyethyl)uridine, and 2'-deoxy-2'-alpha-C-(2,3-dihydroxypropyl)uridine, have been prepared. Conversion of these nucleosides to their appropriately protected phosphoramidites, followed by tetrazole-induced reaction with 2',3'-di-O-acetyluridine, oxidation, and subsequent deprotection furnished the corresponding dinucleoside monophosphates. During the oxidation of the amide-derived phosphite, partial dehydration occurred to give a mixture of the amide- and nitrile-containing dimers. Interestingly, the ratio of amide to nitrile could be largely controlled by choice of oxidant. The hydroxyethyl- and dihydroxypropyl-modified dimers were particularly resistant to snake venom phosphodiesterase-catalyzed hydrolysis (relative half-lives of 129 and 120, respectively, in comparison to UpU). It is anticipated that these nucleoside analogues will ultimately be used in the construction of ribozymes containing enhanced functionality and nuclease resistance.