2,6-diaminopurine riboside | 2140-20-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 2,6-diaminopurine riboside
• 英文别名: 1-(2,6-diamino-purin-7-yl)-β-D-1-deoxy-ribofuranose；(2R,3R,4S,5R)-2-(2,6-diaminopurin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol；(2R,3R,4S,5R)-2-(2,6-diaminopurin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 2140-20-7
• 化学式: C₁₀H₁₄N₆O₄
• 分子量: 282.259
• InChiKey: FJOPVJGCXAWFEC-UUOKFMHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  166
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  尿嘧啶核苷 、 2,6-二氨基嘌呤 在 Citrobacter koseri 作用下， 以 aq. phosphate buffer 为溶剂， 反应 4.0h， 以71%的产率得到2,6-diaminopurine riboside
  参考文献：
  名称：

  Use of Citrobacter koseri whole cells for the production of arabinonucleosides: A larger scale approach

  摘要：

  Purine arabinosides are well known antiviral and antineoplastic drugs. Since their chemical synthesis is complex, time-consuming, and polluting, enzymatic synthesis provides an advantageous alternative. In this work, we describe the microbial whole cell synthesis of purine arabinosides through nucleoside phosphorylase-catalyzed transglycosylation starting from their pyrimidine precursors. By screening of our microbial collection, Citrobacter koseri (CECT 856) was selected as the best biocatalyst for the proposed biotransformation. In order to enlarge the scale of the transformations to 150 mL for future industrial applications, the biocatalyst immobilization by entrapment techniques and its behavior in different reactor configurations, considering both batch and continuous processes, were analyzed. C koseri immobilized in agarose could be used up to 68 times and the storage stability was at least 9 months. By this approach, fludarabine (58% yield in 14h), vidarabine (71% yield in 26h) and 2,6-diaminopurine arabinoside (77% yield in 24h), were prepared. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.procbio.2012.08.011

文献信息

• Use of Citrobacter koseri whole cells for the production of arabinonucleosides: A larger scale approach
  作者：Matías Nóbile、Rosario Médici、Marco Terreni、Elizabeth S. Lewkowicz、Adolfo M. Iribarren

  DOI：10.1016/j.procbio.2012.08.011

  日期：2012.12

  Purine arabinosides are well known antiviral and antineoplastic drugs. Since their chemical synthesis is complex, time-consuming, and polluting, enzymatic synthesis provides an advantageous alternative. In this work, we describe the microbial whole cell synthesis of purine arabinosides through nucleoside phosphorylase-catalyzed transglycosylation starting from their pyrimidine precursors. By screening of our microbial collection, Citrobacter koseri (CECT 856) was selected as the best biocatalyst for the proposed biotransformation. In order to enlarge the scale of the transformations to 150 mL for future industrial applications, the biocatalyst immobilization by entrapment techniques and its behavior in different reactor configurations, considering both batch and continuous processes, were analyzed. C koseri immobilized in agarose could be used up to 68 times and the storage stability was at least 9 months. By this approach, fludarabine (58% yield in 14h), vidarabine (71% yield in 26h) and 2,6-diaminopurine arabinoside (77% yield in 24h), were prepared. (C) 2012 Elsevier Ltd. All rights reserved.