uridine 5'-monobutyrate | 111933-86-9

• 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: uridine 5'-monobutyrate
• 英文别名: [(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl butanoate
• CAS: 111933-86-9
• 化学式: C₁₃H₁₈N₂O₇
• 分子量: 314.295
• InChiKey: TYXCUKNZAWEEGG-FAQVLOEFSA-N

物化性质

• 密度：
  1.443±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  正丁酸乙烯酯 、 尿嘧啶核苷 在 proleather enzyme 作用下， 以 吡啶 为溶剂， 反应 24.0h， 以88%的产率得到uridine 5'-monobutyrate
  参考文献：
  名称：

  通过溶剂工程操纵酶的区域选择性：5'-O-酰基核糖核苷的酶促合成

  摘要：

  酶的区域选择性可以通过溶剂工程来控制。通过这种技术，开发了一种简单方便的方法，用于通过无水吡啶中核糖核苷的伯羟基的蛋白酶催化的区域选择性酯化来高产率地合成5'-O-酰基核糖核苷。

  DOI：

  10.1016/s0040-4039(00)76216-2

文献信息

• [EN] ACYL RIBONUCLEOSIDES AND ACYL DEOXYRIBONUCLEOSIDES<br/>[FR] RIBONUCLEOSIDES D'ACYLE ET DESOXYRIBONUCLEOSIDES D'ACYLE
  申请人：COGNIS IP MAN GMBH

  公开号：WO2005049633A1

  公开（公告）日：2005-06-02

  The present invention is concerned with acyl ribonucleosides and with acyl deoxyribonucleosides. It is furthermore concerned with an enzymatic process for the manufacture of acyl ribonucleosides and of acyl deoxyribonucleosides. It is furthermore concerned with the use of acyl ribonucleosides and of acyl deoxyribonucleosides for cosmetic and for pharmaceutical purposes and with their use as a food supplement for humans or animals. It is furthermore concerned with compositions containing acyl ribonucleosides and acyl deoxyribonucleosides, whereby these compositions are suitable for cosmetic or for pharmaceutical purposes or as food supplement.

  本发明涉及酰基核糖核苷和酰基脱氧核糖核苷。此外，本发明还涉及一种用于制造酰基核糖核苷和酰基脱氧核糖核苷的酶法过程。此外，本发明还涉及酰基核糖核苷和酰基脱氧核糖核苷在化妆品和药品中的用途，以及它们作为人类或动物的食品补充剂的用途。此外，本发明还涉及含有酰基核糖核苷和酰基脱氧核糖核苷的组合物，这些组合物适用于化妆品或药品或作为食品补充剂。
• 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.
• Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide
  作者：Sergio. Riva、Joel. Chopineau、A. P. G. Kieboom、Alexander M. Klibanov

  DOI：10.1021/ja00210a045

  日期：1988.1
• ACYL RIBONUCLEOSIDES AND ACYL DEOXYRIBONUCLEOSIDES
  申请人：Cognis IP Management GmbH

  公开号：EP1680435A1

  公开（公告）日：2006-07-19
• Acyl ribonucleosides and acyl deoxyribonucleosides, compositions of, and methods of making same
  申请人：Kempers Peter

  公开号：US20070160554A1

  公开（公告）日：2007-07-12

  The present invention is concerned with acyl ribonucleosides and with acyl deoxyribonucleosides. It is furthermore concerned with an enzymatic process for the manufacture of acyl ribonucleosides and of acyl deoxyribonucleosides. It is furthermore concerned with the use of acyl ribonucleosides and of acyl deoxyribonucleosides for cosmetic and for pharmaceutical purposes and with their use as a food supplement for humans or animals. It is furthermore concerned with compositions containing acyl ribonucleosides and acyl deoxyribonucleosides, whereby these compositions are suitable for cosmetic or for pharmaceutical purposes or as food supplement.