9-(2-deoxy-β-D-threo-pentofuranosyl)guanine | 116002-28-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(2-deoxy-β-D-threo-pentofuranosyl)guanine
• 英文别名: 2-Amino-9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one；2-amino-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 116002-28-9
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 267.244
• InChiKey: YKBGVTZYEHREMT-HSUXUTPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19
• 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：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-(2-deoxy-β-D-threo-pentofuranosyl)guanine 在 4-二甲氨基吡啶 、 叠氮化锂 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 89.0h， 生成 5'-O-benzoyl-3'-azido-2',3'-dideoxyguanosine
  参考文献：
  名称：

  Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides

  摘要：

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.

  DOI：

  10.1021/jm00118a033
• 作为产物：
  描述：

  鸟苷 在 氨 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 生成 9-(2-deoxy-β-D-threo-pentofuranosyl)guanine
  参考文献：
  名称：

  Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides

  摘要：

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.

  DOI：

  10.1021/jm00118a033

文献信息

• Origin of Difference between One-Electron Redox Potentials of Guanosine and Guanine:  Electrochemical and Quantum Chemical Study
  作者：Jan Langmaier、Zdeněk Samec、Eva Samcová、Pavel Hobza、David Řeha

  DOI：10.1021/jp0481207

  日期：2004.10.1

  voltammetry was used to measure the rates of the chemical oxidation of guanine (G), guanosine (Gs), 2‘-deoxyguanosine (dG), and 2‘-deoxyguanosine 5‘-monophosphate (dGMP) by electrochemically generated tris(2,2‘-bipyridyl)ruthenium(III). The numeric fit of voltammograms to an ECCCE type of mechanism provided the equilibrium and rate constants of the two-step chemical oxidation of the guanine species. One-electron

  循环伏安法用于测量鸟嘌呤 (G)、鸟苷 (Gs)、2'-脱氧鸟苷 (dG) 和 2'-脱氧鸟苷 5'-一磷酸 (dGMP) 的化学氧化速率，通过电化学生成 tris(2, 2'-联吡啶基）钌（III）。伏安图与 ECCCE 类型机制的数值拟合提供了鸟嘌呤物质的两步化学氧化的平衡和速率常数。从第一个电子吸收的平衡常数评估的单电子氧化还原电位遵循序列 G < Gs ≈ dG ≈ dGMP，表明鸟嘌呤最容易被氧化。该序列以速率常数表示，显然遵循预期的驱动力依赖性。使用具有 6-31G** 和 6-31++G** 基组的 DFT/B3LYP 方法进行从头算分子轨道计算，以及具有cc-pVDZ基组的RI-MP2方法，以阐明影响氧化还原电位的各种因素的作用。理论结果表明，差异...
• FUNCTIONAL MOLECULE, FUNCTIONAL MOLECULE SYNTHESIZING AMIDITE AND TARGET SUBSTANCE ANALYSIS METHOD
  申请人：Fujihara Tsuyoshi

  公开号：US20130017973A1

  公开（公告）日：2013-01-17

  To provide a functional molecule including a modified nucleotide unit having a substituent introduced to a base thereof, wherein the substituent is removably introduced to the base; a functional molecule synthesizing amidite that has a substituent removably introduced to its base and that is used for the manufacture of the functional molecule; and a target substance analysis method including: preparing a random pool of functional molecules using a functional molecule synthesizing amidite; screening a functional molecule having affinity for a target substance from the random pool; amplifying the functional molecules having affinity for the target substance, wherein the method further comprises, prior to the amplification step, removing a substituent from the functional molecule having affinity for the target substance.

  提供一种包括具有引入基团的修饰核苷酸单元的功能分子，其中该基团可被可拆卸地引入到基部；一种合成酰胺基的功能分子合成物，其具有可拆卸地引入到其基部的基团，并用于制造功能分子；以及一种目标物质分析方法，包括：使用功能分子合成酰胺基准备功能分子的随机池；从随机池中筛选出与目标物质有亲和力的功能分子；扩增具有与目标物质有亲和力的功能分子，其中该方法在扩增步骤之前还包括从具有与目标物质有亲和力的功能分子中去除基团。
• Study on disulfur-backboned nucleic acids: Part IV. Efficient synthesis of 3′,5′-dithio-2′-deoxyguanosine
  作者：Pei Hua Shang、Chang Mei Cheng、Hua Wang、Hong Chao Zheng、Yu Fen Zhao

  DOI：10.1016/j.cclet.2009.10.017

  日期：2010.2

  Abstract An efficient and novel method for synthesizing 3′,5′-dithio-2′-deoxyguanosine was described. In this method normal guanosine was used as the starting material. A very efficient procedure was used to synthesize 2- O -tosylguanosine 1 , which used 0.1 eq. DBTO instead of 2 eq. 1 was treated with LTBH to give 9-(2-deoxy- β - d -threo-pentofuranosyl)guanine 2 . 2 could be easily turned to the

  摘要描述了一种高效，新颖的3'，5'-二硫代-2'-脱氧鸟苷合成方法。在这种方法中，将正常的鸟苷用作起始原料。使用非常有效的程序来合成2-O-甲苯磺酰鸟苷1，其使用0.1eq.。DBTO代替2 eq。用LTBH处理1，得到9-（2-脱氧-β-d-苏-五氟呋喃糖基）鸟嘌呤2。2可以轻松地转化为目标化合物。
• Deoxygenative [1,2]-Hydride Shift Rearrangements in Nucleoside and Sugar Chemistry:  Analogy with the [1,2]-Electron Shift in the Deoxygenation of Ribonucleotides by Ribonucleotide Reductases¹
  作者：Morris J. Robins、Ireneusz Nowak、Stanislaw F. Wnuk、Fritz Hansske、Danuta Madej

  DOI：10.1021/jo071102b

  日期：2007.10.1

  semipinacol rearrangement that was observed in our laboratory has been applied to the synthesis of several furanose and pyranose derivatives. The process consists of an “orchestrated” [1,2]-hydride shift with departure of a leaving group from the opposite face. Transient formation of a CO group is followed by rapid transfer of a hydride-equivalent from the same face from which the leaving group departed

  在我们的实验室中观察到的半频哪醇重排的变体已应用于几种呋喃糖和吡喃糖衍生物的合成。该过程包括“精心策划的” [1,2]氢化物转移，同时离去基团从相反的表面离开。瞬态形成C O基团后，从离去基团离开的同一面快速转移氢化物当量，这导致两个邻位碳原子处的立体化学两次反转。2'治疗ö -和3'- ö -tosyladenosine与三乙基硼锂在DMSO / THF给出了与β-相应2'-和3'-脱氧核苷类似物d -苏型配置。相同的5'- O处理-TPS -2'- ö -tosyladenosine得到9-（5- ö -TPS-2-脱氧β- d -苏-pentofuranosyl）腺嘌呤。5'-OH和5'- O - TPS化合物具有相同的[1,2]-氢化物位移和立体化学，表明不存在远端羟基参与。将该方法应用于其他核苷2'- O-甲苯磺酰基衍生物，以良好的收率得到了2'-脱氧苏糖基化合物。对于2'- O
• Xylose-DNA Containing the Four Natural Bases
  作者：Frank Seela、Maximilian Heckel、Helmut Rosemeyer

  DOI：10.1002/hlca.19960790518

  日期：1996.8.7

  Oligonucleotides containing (2′-deoxy-β-D-xylofuranosyl)guanine have been prepared. For this purpose 2-aminoadenosine (5) was synthesized and converted to 2′-deoxy-β-D-xyloguanosine (1). The related 2′-deoxy-β-D-xyloisoguanosine (3) and 2′-deoxy-β-D-xyloxanthosine (4) were also synthesized. Compound 1 was converted to the phosphonate and phosphoramidite building blocks 10 and 11, respectively. The

  已经制备了含有（2'-脱氧-β-D-木呋喃糖基）鸟嘌呤的寡核苷酸。为此目的，合成了2-氨基腺苷（5）并将其转化为2'-脱氧-β-D-木葡糖苷（1）。还合成了相关的2'-脱氧-β-D-木基异鸟苷（3）和2'-脱氧-β-D-木基黄嘌呤（4）。化合物1分别转化为膦酸酯和亚磷酰胺结构单元10和11。寡脱氧核苷酸（5'-3'）d（xG-xT-xA-xG-xA-xA-xT-xT-xC-xT-xA-xC-T）（18）形成一个双链体，其T m与亲本（5′-3′）-（GTAGAATTCTAC）（19），但CD频谱倒置。