3'-O-acetyl-N2-isobutyryl-2'-deoxyguanosine | 74925-81-8

• 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: 3'-O-acetyl-N2-isobutyryl-2'-deoxyguanosine
• 英文别名: N-Isobutyryl-3'-O-acetyl-2'-deoxyguanosine；[(2R,3S,5R)-2-(hydroxymethyl)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] acetate
• CAS: 74925-81-8
• 化学式: C₁₆H₂₁N₅O₆
• 分子量: 379.373
• InChiKey: BRWRDMMDQJQLQS-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-N2-isobutyryl-2'-deoxyguanosine 在 吡啶 、 tris(tetra-n-butylammonium) hydrogen pyrophosphate 、 sulfur 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 18.0h， 生成 N-[9-[(2R,4S,5R)-4-acetyloxy-5-[[hydroxy-[hydroxy(phosphonatooxy)phosphoryl]oxy-sulfidophosphaniumyl]oxymethyl]oxolan-2-yl]-6-oxidopurin-2-yl]-2-methylpropanimidate
  参考文献：
  名称：

  Synthesis of Nucleoside α-Thiotriphosphates via an Oxathiaphospholane Approach^†

  摘要：

  Nucleoside 5 '-O-(alpha-thiotriphosphates) were obtained in reactions of the appropriate nucleoside 5 '-O-(2-thio-1,3,2-oxathiaphospholanes) with pyrophosphate in the presence of DBU. The presented method allows also for preparation of alpha-seleno congeners and corresponding a-modified diphosphates.

  DOI：

  10.1021/ol050617r
• 作为产物：
  描述：

  N2-异丁酰-5'-O-(4,4'-二甲氧基三苯基)-2'-脱氧鸟苷 在 吡啶 、 溶剂黄146 作用下， 生成 3'-O-acetyl-N2-isobutyryl-2'-deoxyguanosine
  参考文献：
  名称：

  2-(4-Nitrophenyl)ethyl Methylenebis(phosphonate):  A Versatile Reagent for the Synthesis of Nucleoside 5‘-Methylenebis(phosphonate)s

  摘要：

  2-(4-Nitrophenyl)ethyl methylenebis(phosphonate) (6) was prepared by reaction of equimolar amounts of 2-(4-nitrophenyl)ethyl alcohol and methylenebis(phosphonyl) tetrachloride in the presence of tetrazole. Compound 6 was further converted into the corresponding 4-nitrophenylethyl trisanhydride intermediate 7 by dehydration with diisopropylcarbodiimide (DIC). Reaction of 7 with either 2',3'-O-isopropylideneadenosine (8a) or 2',3'-O-isopropylideneguanosine (8b) afforded, after hydrolysis, the desired P-1-[2-(4-nitrophenyl)ethyl]-P-2-(2',3'-O-isopropylideneadenosin-5'-yl)methylenebis(phosphonate) (9a) and guanosine analogue 9b, respectively. A similar treatment of intermediate 7 with 3'-O-acetylthymidine (12a), 3'-O-acetyl-2'-deoxy-N-4-benzoylcytidine (12b), 3'-O-acetyl-2'-deoxy-N-6-benzoyladenosine (12c), and 3'-O-acetyl-2'-deoxy-N-2-isobutyrylguanosine (12d) gave the corresponding 2-(4-nitrophenyl)ethyl methylenebis(phosphonate)s 13a-d. These compounds as well as 9a,b were treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) which caused elimination of the 2-(4-nitrophenyl)ethyl group. The base labile 3'-O-acetyl, N-4-acetyl, N-6-benzoyl, and N-2-isobutyryl groups of 12a-d were also removed during the DBU treatment. Thus, the 5'-methylenebis(phosphonate)s of 2',3'-O-isopropylideneadenosine (10a), 2',3'-O-isopropylideneguanosine (10b), thymidine (14a), 2'-deoxycytidine (14b), 2'-deoxyadenosine (14c), and 2'-deoxyguanosine (14d) were prepared in good yield. De-O-isopropylidenation of 10a and 10b afforded adenosine 5'-methylenebis(phosphonate) (11a) and guanosine 5'-methylenebis(phosphonate) (11b), respectively.

  DOI：

  10.1021/jo971859a

文献信息

• [EN] METHOD FOR FLUORESCENCE LABELING OF BIOLOGICAL MATERIALS, THERMALLY REMOVABLE FLUORESCENT LABELS FOR THIS METHOD, AND METHODS OF THEIR PREPARATION AND USE<br/>[FR] PROCÉDÉ DE MARQUAGE PAR FLUORESCENCE DE MATÉRIAUX BIOLOGIQUES, MARQUEURS FLUORESCENTS ÉLIMINABLES PAR VOIE THERMIQUE DESTINÉS À CE PROCÉDÉ ET LEURS PROCÉDÉS DE PRÉPARATION ET D'UTILISATION
  申请人：FUTURESYNTHESIS SPOLKA Z O O

  公开号：WO2020117079A1

  公开（公告）日：2020-06-11

  The compounds (12), (13) of the invention are applied as thermosensitive fluorescent labels for labeling of biological material with fluorescent dyes used for biological, chemical or physical analyzes. Disclosed is also a method for fluorescence labeling of nucleosides, nucleotides and oligonucleotides with those fluorescent dyes characterized in that a moiety of general formula 1 or 2 or 3 or 4 with the double bond configuration E is attached to a nucleoside nucleotide or oligonucleotide.

  本发明的化合物（12），（13）被应用为热敏荧光标记物，用于使用于生物、化学或物理分析的荧光染料对生物材料进行标记。还公开了一种荧光标记核苷、核苷酸和寡核苷酸的方法，其中这些荧光染料的特征是将通式1或2或3或4的基团与具有双键构型E的核苷、核苷酸或寡核苷酸结合。
• [EN] THERMALLY-CLEAVABLE PROTECTING AND LINKER GROUPS<br/>[FR] GROUPES PROTECTEURS ET DE LIAISON THERMIQUEMENT CLIVABLES
  申请人：EVONETIX LTD

  公开号：WO2018189546A1

  公开（公告）日：2018-10-18

  The present invention relates to chemical linkers and protecting groups, compounds and compositions containing the chemical linkers or protecting groups, and intermediates and processes that can be used to prepare them. The chemical linkers and protecting groups are based on pyrrolidine and piperidine activating groups, which undergo intramolecular cyclisation upon heating with release of carbon dioxide, thereby releasing the organic compound from a substrate. In particular, those chemical linkers and protecting groups are useful in the solid phase synthesis of oligonucleotides according to the following representative schemes.

  本发明涉及化学连接剂和保护基团，含有化学连接剂或保护基团的化合物和组合物，以及可用于制备它们的中间体和过程。这些化学连接剂和保护基团基于吡咯烷和哌哆啶活化基团，加热后发生分子内环化，并释放二氧化碳，从而释放有机化合物从底物中。特别是，这些化学连接剂和保护基团在寡核苷酸的固相合成中具有用途，具体方案如下。
• SYNTHESES OF NOVEL SUBSTITUTED-BORANOPHOSPHATE NUCLEOSIDES
  作者：Kamesh Vyakaranam、Geeta Rana、Bernard F. Spielvogel、John A. Maguire、Narayan S. Hosmane

  DOI：10.1081/ncn-120015070

  日期：2002.11

  cyano, carboxy, or carbamoyl) borano] deoxynucleosides (3a-4c) and 5'-[diethylphosphite(cyano or carboxy) borano] deoxynucleosides (6a-7d) were prepared by a variety of synthetic procedures. The syntheses of the pyrophosphates (2a-2c), as precursors for 3a-4c, are also described.

  许多取代的（硼烷）核酸，3'-[亚磷酸二乙酯（氰基，羧基或氨基甲酰基）硼烷]脱氧核苷（3a-4c）和5'-[亚磷酸二乙酯（氰基或羧基）硼烷]脱氧核苷（6a-7d）通过各种合成程序制备。还描述了作为3a-4c的前体的焦磷酸盐（2a-2c）的合成。
• Synthesis of α-P-Modified Nucleoside Diphosphates with Ethylenediamine
  作者：Ping Li、Zhihong Xu、Hongyan Liu、Charlotta K. Wennefors、Mikhail I. Dobrikov、János Ludwig、Barbara Ramsay Shaw

  DOI：10.1021/ja055179y

  日期：2005.12.1

  a one-pot synthesis of α-P-borano-, α-P-thio-, and α-P-seleno-modified nucleoside diphosphate analogues that are otherwise difficult to obtain. The key step involves the intramolecular nucleophilic attack by an amino group in 5 to remove the γ-phosphate. The absolute configurations of P-diastereomers were confirmed by analysis of their 1H NMR. Affinity studies revealed that the nucleoside boranodiphosphates

  本报告描述了 α-P-硼烷-、α-P-硫代-和 α-P-硒修饰的核苷二磷酸类似物的一锅合成，否则很难获得。关键步骤涉及 5 中的氨基进行分子内亲核攻击以去除 γ-磷酸盐。P-非对映异构体的绝对构型通过其 1H NMR 分析得到证实。亲和力研究表明，核苷硼二磷酸在抗病毒研究中可能有用。
• Acid–base properties of the nucleic-acid model 2′-deoxyguanylyl(5′→3′)-2′-deoxy-5′-guanylate, d(pGpG)3–, and of related guanine derivatives
  作者：Bernd Knobloch、Helmut Sigel、Andrzej Okruszek、Roland K. O. Sigel

  DOI：10.1039/b517904a

  日期：——

  detail. In this study the six deprotonation reactions of H4[d(pGpG)]+ are quantified. The acidity constants for the release of the first proton from the terminal P(O)(OH)2 group (pKa = 0.65) and for one of the (N7)H+ sites (pKa = 2.4) are estimated. The acidity constants of the remaining four deprotonation reactions were measured by potentiometric pH titrations in aqueous solution (25 degrees C; I =

  二核苷酸d（pGpG）是一种常用的DNA模型，用于研究DNA与金属离子之间的各种相互作用，但其酸碱性质尚未详细描述。在这项研究中，对H4 [d（pGpG）] +的六个去质子化反应进行了定量。估计了从末端P（O）（OH）2基团释放出第一质子的酸度常数（pKa = 0.65），以及一个（N7）H +位点（pKa = 2.4）的酸度常数。其余四个去质子化反应的酸度常数是通过在水溶液（25摄氏度； I = 0.1 M，NaNO3）中通过电位pH滴定法测量的：第二个（N7）H +，P（O）的去质子化的pKa值2（OH）-，两个（N1）H位分别为2.98、6.56、9.54和10.11。基于这些结果，我们显示了如何估算尚未研究的相关系统的酸度常数，例如 pGpG，它参与轮状病毒RNA聚合酶的起始步骤。简要指出了我们的研究结果与核酸的相关性。