2'-O, 3'-O, N²-triisobutyrylguanosine | 56489-75-9

• 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: 2'-O, 3'-O, N²-triisobutyrylguanosine
• 英文别名: (2R,3R,4R,5R)-2-(hydroxymethyl)-5-(2-isobutyramido-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl bis(2-methylpropanoate)；Guanosine, N-(2-methyl-1-oxopropyl)-, 2',3'-bis(2-methylpropanoate)；[(2R,3R,4R,5R)-2-(hydroxymethyl)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]-4-(2-methylpropanoyloxy)oxolan-3-yl] 2-methylpropanoate
• CAS: 56489-75-9
• 化学式: C₂₂H₃₁N₅O₈
• 分子量: 493.517
• InChiKey: JJRMTPVXETZPOA-QEPJRFBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2'-O, 3'-O, N²-triisobutyrylguanosine 在 potassium dihydrogenphosphate 作用下， 生成 Phosphoric acid (2R,3S,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 6-(3-{2-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethyldisulfanyl}-propionylamino)-hexyl ester
  参考文献：
  名称：

  Synthesis, incorporation efficiency, and stability of disulfide bridged functional groups at RNA 5′-ends

  摘要：

  Modified guanosine monophosphates have been employed to introduce various functional groups onto RNA 5'-ends. Applications of modified RNA 5'-ends include the generation of functionalized RNA libraries for in vitro selection of catalytic RNAs, the attachment of photoaffinity-tags for mapping RNA-protein interactions or active sites in catalytic RNAs, or the nonradioactive labeling of RNA molecules with fluorescent groups. While in these and in similar applications a stable linkage is desired, in selection experiments for generating novel catalytic RNAs it is often advantageous that a functional group is introduced reversibly. Here we give a quantitative comparison of the different strategies that can be applied to reversibly attach functional groups via disulfide bonds to RNA 5'-ends. We report the preparation of functional groups with disulfide linkages, their incorporation efficiency into an RNA library, and their stability under various conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00080-8
• 作为产物：
  描述：

  2'-O,3'-O,N2-triisobutyryl-5'-O-(4,4'-dimethoxytrityl)guanosine 在 吡啶 、 三氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以49%的产率得到2'-O, 3'-O, N²-triisobutyrylguanosine
  参考文献：
  名称：

  Synthesis of guanosine 5′-conjugates and their use as initiator molecules for transcription priming

  摘要：

  我们合成了两种与生物素化腺苷部分相连的鸟苷衍生物，采用了两种不同的策略，一种是在固相上进行合成步骤，另一种则完全在溶液中进行。合成的衍生物在转录引物实验中被证明可以作为引发分子使用。引入效率被确定为大约2%。尽管这个值相对较低，但在选择实验中使用其中任何一种分子似乎都是合理的。基本上，可以生成序列复杂度为10^15到10^16的RNA文库。用我们的引发分子标记这样的文库仍然可以产生10^13到10^14个标记/功能化序列，从而提供足够的序列空间用于选择。

  DOI：

  10.1039/b716151d

文献信息

• Studies on transfer ribonucleic acids and related compounds. XXXIV. Stepwise diester or partial triester synthesis of penta- to octanucleotides corresponding to residues 41-46, 47-54, 61-65 and 66-71 of tRNAfMet of E. coli.
  作者：EIKO OHTSUKA、TETSUO MIYAKE、EIKO NAKAGAWA、MORIO IKEHARA、ALEXANDER F. MARKHAM

  DOI：10.1248/cpb.28.2450

  日期：——

  A hexanucleotide and an octanucleotide corresponding to tRNAMetf bases 41-46 and 47-54 were synthesized by stepwise addition of mononucleotides. The octanucleotide is the largest oligoribonucleotide synthesized by this method. A pentanucleotide (bases 61-65) and a hexanucleotide (bases 66-71) were synthesized via partially triesterified intermediates. The deblocked products were purified by ion-exchange chromatography and characterized by enzymatic hydrolysis. These oligonucleotides were used as substrates in joining reactions with RNA ligase.

  通过逐步添加单核苷酸，合成了对应于tRNAMetf第41-46位和第47-54位的六核苷酸和八核苷酸。这个八核苷酸是通过这种方法合成的最大的寡核糖核酸。通过部分三酯化中间体，合成了一个五核苷酸（第61-65位）和一个六核苷酸（第66-71位）。去阻断产物通过离子交换色谱法进行纯化，并利用酶解法进行表征。这些寡核苷酸被用作RNA连接酶连接反应中的底物。
• [EN] TRANSLATIONAL ENHANCERS AND RELATED METHODS<br/>[FR] AMPLIFICATEURS DE TRADUCTION ET PROCÉDÉS ASSOCIÉS
  申请人：EFFECTOR THERAPEUTICS INC

  公开号：WO2021001739A1

  公开（公告）日：2021-01-07

  The present disclosure relates to novel translational enhancers comprising an eukaryotic initiation factor 4E (eIF4E) ligand attached to a dinucleotide. The present disclosure also relates to RNA molecules (e.g., mRNAs) comprising the novel translational enhancers, which imparts properties to the RNA molecules that are advantageous to therapeutic development, methods of using RNA molecules comprising such novel translational enhancers for therapeutic uses, as well as kits containing the translational enhancers.

  本公开涉及包含连接到二核苷酸的真核起始因子4E（eIF4E）配体的新型转译增强剂。本公开还涉及包含这些新型转译增强剂的RNA分子（例如mRNA），这些RNA分子赋予了对治疗开发有利的特性，以及使用包含这些新型转译增强剂的RNA分子进行治疗用途的方法，以及包含转译增强剂的试剂盒。
• A modified dinucleotide for site-specific RNA-labelling by transcription priming and click chemistry
  作者：Ayan Samanta、André Krause、Andres Jäschke

  DOI：10.1039/c3cc46132g

  日期：——

  An improved strategy for RNA labelling using an alkyne-carrying dinucleotide is reported. This involves near-quantitative priming by phage RNA-polymerases followed by conjugation of different labels using click chemistry. Moreover, these transcripts bear a ligation compatible 5′-end, and thus through ligation the terminal label can be transformed to an internal one.

  报告中介绍了一种使用炔烃载体二核苷酸进行 RNA 标记的改进策略。这种方法是先用噬菌体 RNA 聚合酶进行近定量的引物处理，然后用点击化学法连接不同的标签。此外，这些转录本的 5′端与连接兼容，因此可以通过连接将末端标签转化为内部标签。
• Site-specific modification of enzymatically synthesized RNA: Transcription initiation and Diels-Alder reaction
  作者：Burckhard Seelig、Andres Jäschke

  DOI：10.1016/s0040-4039(97)10151-4

  日期：1997.11

  Initiator nucleotides consisting of an anthracene ring system coupled to the 5'-phosphate of guanosine monophosphate via a polyethylene glycol (PEG) linker were chemically synthesized. When added to transcription reactions, these initiators were site-specifically incorporated into RNA transcripts yielding RNA conjugates with a fluorophore selectively attached to the 5'-end via a flexible linker. Besides sensitive fluorescence detection, the anthracene allowed the convenient modification with maleimides by Diels-Alder reaction. (C) 1997 Elsevier Science Ltd.