thymidine 3'-butyrate | 132216-93-4

• 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: thymidine 3'-butyrate
• 英文别名: [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] butanoate
• CAS: 132216-93-4
• 化学式: C₁₄H₂₀N₂O₆
• 分子量: 312.323
• InChiKey: GWVBOBYCKWACFZ-HBNTYKKESA-N

物化性质

• 熔点：
  146-148 °C
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Acetoneoxime butyrate 、 beta-胸苷 在 Amano PS Lipase 作用下， 以 吡啶 为溶剂， 反应 48.0h， 以74%的产率得到thymidine 3'-butyrate
  参考文献：
  名称：

  Regioselective Acylation of 2′-Deoxynucleosides Through an Enzymatic Reaction with Oxime Esters

  摘要：

  使用肟酯作为酰基转移剂，通过酶促反应可获得 2′-脱氧核苷的 3′-O-酰基衍生物，收率很高。

  DOI：

  10.1055/s-1992-26178

文献信息

• Controlling Subtilisin Activity and Selectivity in Organic Media by Imprinting with Nucleophilic Substrates
  作者：Joseph O. Rich、Jonathan S. Dordick

  DOI：10.1021/ja9637715

  日期：1997.4.1

  The activity and substrate specificity of subtilisin-catalyzed acylation of nucleosides in organic solvents can be controlled by lyophilizing the enzyme from an aqueous solution containing the substrate. This “molecular imprinting” technique was examined using thymidine as a model nucleoside, and the resulting subtilisin preparation was up to 50-fold more reactive toward thymidine acylation in nearly

  枯草杆菌蛋白酶催化的有机溶剂中核苷酰化的活性和底物特异性可以通过从含有底物的水溶液中冻干酶来控制。这种“分子印迹”技术使用胸苷作为模型核苷进行检测，所得枯草杆菌蛋白酶制剂在几乎无水四氢呋喃中对胸苷酰化的反应比在没有核苷的情况下从水性缓冲液中冻干的枯草杆菌蛋白酶高 50 倍。尽管用枯草杆菌蛋白酶冻干的几种化合物，包括胸腺嘧啶和核糖，提高了胸苷酰化的速率，但胸苷印迹酶是该反应最有效的催化剂。此外，通过在不同亲核底物存在下冻干酶，可以改变枯草杆菌蛋白酶的底物选择性。例如，印记使得区分结构不同（即蔗糖与胸苷）以及结构不同成为可能。
• A useful and versatile procedure for the acylation of nucleosides through an enzymic reaction
  作者：Francisco Moris、Vicente Gotor

  DOI：10.1021/jo00055a018

  日期：1993.1

  Lipase-mediated acylation of nucleosides with oxime esters in organic solvents has been achieved. Candida antarctica lipases (SP435 and SP435A) showed high regioselectivity toward the primary hydroxyl group of both deoxy- and ribonucleosides, whereas other lipases exhibited poor results for this goal. 2'-Deoxynucleosides, such as thymidine and 2'-deoxyadenosine, were acylated with oxime esters carrying saturated, unsaturated, aromatic, and functionalized chains, giving 5'-O-acylated compounds together with small quantities of the 3'-O-acylated regioisomer. Uridine, adenosine, and inosine, as representative ribonucleosides, were acylated exclusively at the 5'-OH by using the same methodology. Nucleosides bearing a cytosine ring were found to be unreactive with oxime esters under the same conditions. 2'-Deoxycytidine was acylated with acid anhydrides and C. antarctica lipase to give N,5'-O-diacylated compounds, whereas cytidine gave mixtures, reason for which it had to be previously chemically N-acylated and then subjected to the oxime esters and lipase, giving the same results as ribonucleosides.
• RONCO, GINO LINO;VILLA, PIERRE JOSEPH;VILLE, GUY ANDRE
  作者：RONCO, GINO LINO、VILLA, PIERRE JOSEPH、VILLE, GUY ANDRE

  DOI：——

  日期：——
• Regioselective Acylation of 2′-Deoxynucleosides Through an Enzymatic Reaction with Oxime Esters
  作者：Vicente Gotor、Francisco Morís

  DOI：10.1055/s-1992-26178

  日期：——

  3′-O-Acyl derivatives of 2′-deoxynucleosides are obtained in good yield through an enzymatic reaction using oxime esters as acyl transfer agents.

  使用肟酯作为酰基转移剂，通过酶促反应可获得 2′-脱氧核苷的 3′-O-酰基衍生物，收率很高。