2'-脱氧三氮唑核苷 | 40372-06-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 中文名称: 2'-脱氧三氮唑核苷
• 英文名称: 1-(2'-deoxy-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide
• 英文别名: 2'-deoxyribavirin；1-(β-D-erythro-2-deoxy-pentofuranoyl)-1H-[1,2,4]triazole-3-carboxylic acid amide；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
• CAS: 40372-06-3
• 化学式: C₈H₁₂N₄O₄
• 分子量: 228.208
• InChiKey: GODSJHAJEWFDAD-KVQBGUIXSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  587.7±60.0 °C(Predicted)
• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-脱氧三氮唑核苷 生成 [(2R,3S,5R)-5-(3-carbamoyl-1,2,4-triazol-1-yl)-3-hydroxyoxolan-2-yl]methyl 4-methylbenzoate
  参考文献：
  名称：

  SANGHVI, YOGESH S.;HANNA, NAEEM B.;LARSON, STEVEN B.;ROBINS, ROLAND K.;RE+, NUCLEOSIDES AND NUCLEOTIDES, 6,(1987) N 4, 761-774

  摘要：

  DOI：
• 作为产物：
  描述：

  利巴韦林 生成 2'-脱氧三氮唑核苷
  参考文献：
  名称：

  Imidazole-4-Carboxamide and 1,2,4-Triazole-3-Carboxamide Deoxynucleotides as Simplified DNA Building Blocks with Ambiguous Pairing Capacity

  摘要：

  2'-Deoxynucleosides of imidazole-4 (or 1,2,4-triazole-3)-carboxamide, ethyl imidazole-4 (or 1,2,4 triazole-3)-carboxylate were synthesized by enzymatic glycosylation using N-deoxyribosyltransferase from a lactobacterium. The base:pairing properties of Y and V when placed opposite the natural DNA bases as well as their self were evaluated by thermal denaturation experiments. DNA templates containing imidazole-4-carboxamide base were used in elongation reaction catalysed by Klenow fragment.

  DOI：

  10.1080/07328319808004740

文献信息

• A Combination Chemical and Enzymatic Approach for the Preparation of Azole Carboxamide Nucleoside Triphosphate
  作者：Weidong Wu、Donald E. Bergstrom、V. Jo Davisson

  DOI：10.1021/jo020745i

  日期：2003.5.1

  biochemical tools. Many of the standard methods for nucleoside triphosphate synthesis fail in the cases of nonpurine and nonpyrimidine nucleosides. An efficient preparation of the 5'-O-tosylates for both the deoxy- and ribonucleosides enabled preparation of the diphosphate esters by displacement with tris(tetra-n-butylammonium) pyrophosphate. Enzymatic synthesis of the azole carboxamide deoxyribonucleoside

  DNA和RNA聚合酶的替代底物提供了一组重要的生化工具。在非嘌呤和非嘧啶核苷的情况下，许多标准的三磷酸核苷合成方法都失败了。有效地制备脱氧核糖核苷和核糖核苷的5'-O-甲苯磺酸酯能够通过用焦磷酸三（四正丁基铵）置换来制备二磷酸酯。ATP的磷酸供体，二磷酸核苷激酶作为催化剂的酶合成吡咯酰胺脱氧核糖核苷三磷酸是基于磷酸烯醇丙酮酸（PEP）和丙酮酸激酶作为ATP再生系统。核糖核苷三磷酸的合成需要PEP作为磷酸供体，丙酮酸激酶作为催化剂。开发了基于硼酸酯亲和力凝胶的优化纯化程序以产生高度纯化的三磷酸核苷。本文概述的策略为制备5'-三磷酸核苷提供了一种新的有效方法，可能适用于多种碱基和糖修饰的核苷类似物。
• <i>Aeromonas hydrophila</i>strains as biocatalysts for transglycosylation
  作者：Matías Nóbile、Marco Terreni、Elizabeth Lewkowicz、Adolfo M. Iribarren

  DOI：10.3109/10242422.2010.538949

  日期：2010.12

  Microbial transglycosylation is useful as a green alternative in the preparation of purine nucleosides and analogues, especially for those that display pharmacological activities. In a search for new transglycosylation biocatalysts, two Aeromonas hydrophila strains were selected. The substrate specificity of both micro-organisms was studied and, as a result, several nucleoside analogues have been prepared. Among them, ribavirin, a broad spectrum antiviral, and the well-known anti HIV didanosine, were prepared, in 77 and 62% yield using A. hydrophila CECT 4226 and A. hydrophila CECT 4221, respectively. In order to scale-up the processes, the reaction conditions, product purification and biocatalyst preparation were analyzed and optimized.
• Development of a nanostabilized biocatalyst using an extremophilic microorganism for ribavirin biosynthesis
  作者：Eliana C. De Benedetti、Cintia W. Rivero、Jorge A. Trelles

  DOI：10.1016/j.molcatb.2015.08.006

  日期：2015.11

  Ribavirin is a guanosine analogue commonly used as an antiviral compound for the treatment of Hepatitis C virus (HCV) infection. The biosynthesis of this compound using Geobacillus kaustophilus ATCC 8005 as biocatalyst is herein reported. This extremophilic microorganism has been successfully entrapped in an agarose matrix supplemented with bentonite, which was defined as bionanocomposite. This immobilized biocatalyst was stable for more than 580 h without activity loss, significantly improving operational stability and mechanical properties over the conventional agarose matrix.Furthermore, a packed-bed bioreactor for bioprocess scale-up was designed, which was able to produce 370 mg L-1 of ribavirin. In conclusion, a smooth, inexpensive and environmentally friendly method to obtain ribavirin was developed in this study. (C) 2015 Elsevier B.V. All rights reserved.
• In Search of New Inhibitors of HIV-1 Replication: Synthesis and Study of 1-(2′-Deoxy-β-D-Ribofuranosyl)-1,2,4-Triazole-3-Carboxamide as a Selective Viral Mutagenic Agent
  作者：V. Vivet-Boudou、J.-C. Paillart、A. Burger、R. Marquet

  DOI：10.1080/15257770701490902

  日期：2007.11.26

  With the emergence of HIV strains resistant or cross-resistant to nearly all antiretroviral regimen, novel therapy approaches have to be considered. As a part of our current work on viral mutagenic compounds, we prepared 1-(2' -deoxy-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide (2' -deoxy-ribavirin) and its 5' -triphosphate derivative. The nucleoside mutagenic activity was evaluated on HIV-1 NL4-3 in CEMx174 cell culture. After 2.5 months, no reduction on HIV-1 viability was observed. On the other hand, in vitro experiments with purified HIV-1 RT demonstrated that the triphosphate analog can be incorporated opposite to several natural nucleosides.
• USRE29835E
  申请人：——

  公开号：USRE29835E

  公开（公告）日：1978-11-14