Decanoic acid (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester | 143601-34-7

• 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: Decanoic acid (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] decanoate
• CAS: 143601-34-7
• 化学式: C₂₀H₃₂N₂O₆
• 分子量: 396.484
• InChiKey: LDRYHJDPAGWCPW-GVDBMIGSSA-N

物化性质

• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  acetone oxime decanoate 、 beta-胸苷 在 Amano PS Lipase 作用下， 以 吡啶 为溶剂， 反应 48.0h， 以83%的产率得到Decanoic acid (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  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

• Influence of substituent groups in regioselective acylation of nucleosides by Novozym 435 lipase
  作者：Zhao-Yu Wang、Yan-Hong Bi、Xiang-Qian Li、Min-Hua Zong

  DOI：10.1016/j.procbio.2013.06.022

  日期：2013.8

  comparative study on the substrate recognition was conducted successfully in Novozym 435-mediated acylation of various 2′- or 5-substituted nucleosides with acyl donors carrying different aliphatic chain lengths (C6, C10, and C14). The unexpected results revealed that the physicochemical property of the substituents (such as the size, hydrophobicity, and substitutional position) in nucleosides profoundly influenced

  在 Novozym 435 介导的各种 2' 或 5 取代核苷与携带不同脂肪链长度（C6、C10 和 C14）的酰基供体的酰化中，成功地进行了底物识别的比较研究。出乎意料的结果表明，核苷中取代基的物理化学性质（如大小、疏水性和取代位置）对酶的行为产生了深远的影响。源自核苷 2'-或 5-位取代基的不同底物结合模式可以解释这一点。此外，除了脂肪酶活性位点的几何构型之外，控制区域选择性的另一个可能因素可能归因于取代基和酰基供体之间的相互作用。
• 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.