4'-thioadenosine 5'-triphosphate | 667882-41-9

• 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: 4'-thioadenosine 5'-triphosphate
• 英文别名: 4'-thioATP；[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxythiolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• CAS: 667882-41-9
• 化学式: C₁₀H₁₆N₅O₁₂P₃S
• 分子量: 523.251
• InChiKey: FULIUACOJJYBQF-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.9
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  295
• 氢给体数：
  7
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  N6-benzoyl-9-(2,3-di-O-acetyl-4-thio-β-D-ribofuranosyl)adenine 在 吡啶 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 、 三正丁胺 、 三丁基焦磷酸铵 、 ammonium hydroxide 、 水 、 碘 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.34h， 生成 4'-thioadenosine 5'-triphosphate
  参考文献：
  名称：

  Investigations toward the selection of fully-modified 4′-thioRNA aptamers: Optimization of in vitro transcription steps in the presence of 4′-thioNTPs

  摘要：

  We describe herein a method for isolating fully-modified 4 '-thioRNA aptamers against human alpha-thrombin using the SELEX protocol. In order to isolate the desired aptamers, in vitro transcription was examined in the presence of four kinds of 4 '-thioribonucleoside triphosphates (4 '-thioNTPs) in an effort to afford the fully-modified 4 '-thioRNA. The transcription efficiency of the 4 '-thioNTPs was first compared with that of the nucleoside 5 '-(alpha-thio)triphosphates (alpha SNTPs) and found to be less effective than that of the aSNTPs, especially when GTP and/or ATP were substituted for 4 '-thioGTP and/or 4 '-thioATP. Further attempts to improve its efficiency, including the use of a mutant RNA polymerase instead of the wild type, various additives, and 4 '-thioNTP concentrations were unsuccessful. Accordingly, the transcription was performed in the presence of 4 '-thioNTPs together with the natural GTP and ATP at the appropriate concentrations. Although this attempt furnished a highly-modified 4 '-thioRNA, but not a fully-modified 4 '-thioRNA, we eventually succeeded in isolating the fully-modified 4 '-thioRNA aptamers by SELEX using optimized transcription conditions, followed by post-modification of the resulting aptamers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.048

文献信息

• [EN] RIBONUCLEIC ACIDs WITH 4'-THIO-MODIFIED NUCLEOTIDES AND RELATED METHODS<br/>[FR] ACIDES RIBONUCLÉIQUES AYANT DES NUCLÉOTIDES 4'-THIO-MODIFIÉS ET PROCÉDÉS ASSOCIÉS
  申请人：SHIRE HUMAN GENETIC THERAPIES

  公开号：WO2014152513A1

  公开（公告）日：2014-09-25

  Disclosed are messenger RNA molecules and related compositions incorporating a 4'-thio modification in the furanose ring of at least one nucleotide residue, and methods of using these mRNAs to produce an encoded therapeutic protein invivo and to treat or prevent diseases or disorders. In certain embodiments, the 4'-thio modified mRNA provides for enhanced stability and/or reduced immunogenicity in in vivo therapies.

  本文揭示了信使RNA分子及相关组合物，其中至少一个核苷酸残基的呋喃糖环中包含4'-硫代修饰，并且使用这些mRNA来在体内产生编码的治疗蛋白质并用于治疗或预防疾病或紊乱的方法。在某些实施例中，4'-硫代修饰的mRNA在体内疗法中提供了增强的稳定性和/或减少的免疫原性。
• 4'-thionucleotide
  申请人：Matsuda Akira

  公开号：US20060127990A1

  公开（公告）日：2006-06-15

  Disclosed is a compound of formula I: [wherein B is a nucleobase selected from the group consisting of adenine, guanine, cytosine, uracil and hypoxanthine], a compound of formula II: [wherein B′ is a nucleobase selected from the group consisting of adenine, guanine, cytosine, thymine, uracil and hypoxanthine], a method for synthesizing these nucleoside triphosphates, and a process for producing an oligonucleotide using these nucleoside triphosphates.

  本发明涉及一种化合物I的配方：[其中B是从腺嘌呤，鸟嘌呤，胞嘧啶，尿嘧啶和次黄嘌呤中选择的核苷碱]，一种化合物II的配方：[其中B'是从腺嘌呤，鸟嘌呤，胞嘧啶，胸腺嘧啶，尿嘧啶和次黄嘌呤中选择的核苷碱]，一种合成这些核苷酸三磷酸盐的方法，以及使用这些核苷酸三磷酸盐制备寡核苷酸的过程。
• RIBONUCLEIC ACIDs WITH 4'-THIO-MODIFIED NUCLEOTIDES AND RELATED METHODS
  申请人：SHIRE HUMAN GENETIC THERAPIES, INC.

  公开号：US20160031928A1

  公开（公告）日：2016-02-04

  Disclosed are messenger RNA molecules and related compositions incorporating a 4′-thio modification in the furanose ring of at least one nucleotide residue, and methods of using these mRNAs to produce an encoded therapeutic protein in vivo and to treat or prevent diseases or disorders. In certain embodiments, the 4′-thio modified mRNA provides for enhanced stability and/or reduced immunogenicity in in vivo therapies.

  本发明涉及一种信使RNA分子及相关组合物，其中至少一个核苷酸残基的呋喃糖环中包含4'-硫修饰，并且使用这些mRNA在体内产生编码的治疗蛋白质并治疗或预防疾病或疾病的方法。在某些实施方式中，4'-硫修饰的mRNA提供了增强的稳定性和/或减少了体内治疗中的免疫原性。
• Ribonucleic acids with 4′-thio-modified nucleotides and related methods
  申请人：TRANSLATE BIO, INC.

  公开号：US10266559B2

  公开（公告）日：2019-04-23

  Disclosed are messenger RNA molecules and related compositions incorporating a 4′-thio modification in the furanose ring of at least one nucleotide residue, and methods of using these mRNAs to produce an encoded therapeutic protein in vivo and to treat or prevent diseases or disorders. In certain embodiments, the 4′-thio modified mRNA provides for enhanced stability and/or reduced immunogenicity in in vivo therapies.

  本发明公开了在至少一个核苷酸残基的呋喃糖环上加入 4′-硫代修饰的信使 RNA 分子和相关组合物，以及使用这些 mRNA 在体内产生编码的治疗性蛋白质和治疗或预防疾病或紊乱的方法。在某些实施方案中，4′-硫代修饰的mRNA可提高体内疗法的稳定性和/或降低免疫原性。
• RIBONUCLEIC ACIDS WITH 4'-THIO-MODIFIED NUCLEOTIDES AND RELATED METHODS
  申请人：TRANSLATE BIO, INC.

  公开号：US20190263850A1

  公开（公告）日：2019-08-29

  Disclosed are messenger RNA molecules and related compositions incorporating a 4′-thio modification in the furanose ring of at least one nucleotide residue, and methods of using these mRNAs to produce an encoded therapeutic protein in vivo and to treat or prevent diseases or disorders. In certain embodiments, the 4′-thio modified mRNA provides for enhanced stability and/or reduced immunogenicity in in vivo therapies.