5-(羟甲基)胞苷 | 19235-17-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 5-(羟甲基)胞苷
• 中文别名: 5-羟甲基胞苷
• 英文名称: 5-hydroxymethylcytidine
• 英文别名: 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(hydroxymethyl)pyrimidin-2-one
• CAS: 19235-17-7
• 化学式: C₁₀H₁₅N₃O₆
• 分子量: 273.246
• InChiKey: NFEXJLMYXXIWPI-JXOAFFINSA-N

物化性质

• 熔点：
  215 °C (decomp)
• 沸点：
  621.1±65.0 °C(Predicted)
• 密度：
  1.92±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（稍微加热）、甲醇（稍微加热）、水（稍微加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  149
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(羟甲基)胞苷 在 manganese(IV) oxide 、 甲酸 作用下， 以 aq. phosphate buffer 、 水 、 甘油 、 乙腈 为溶剂， 反应 1.0h， 生成 4-氨基-1-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]-2-氧代嘧啶-5-甲醛
  参考文献：
  名称：

  The existence of 5-hydroxymethylcytosine and 5-formylcytosine in both DNA and RNA in mammals

  摘要：

  我们开发了一种新的策略，通过氧化衍生化结合质谱分析来确定DNA和RNA中的5-羟甲基胞嘧啶和5-甲酰胞嘧啶。

  DOI：

  10.1039/c5cc07354e
• 作为产物：
  描述：

  胞苷 在 盐酸 、 硫酸 、 水 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 73.5h， 生成 5-(羟甲基)胞苷
  参考文献：
  名称：

  Photo‐Facilitated Detection and Sequencing of 5‐Formylcytidine RNA

  摘要：

  Abstract5‐Formylcytidine (f5C) is one of the epigenetic nucleotides in tRNA. Despite the evident importance of f5C in gene expression regulation, little is known about its exact amount and position. To capture this information, we developed a modification‐specific functionalization with a semi‐stabilized ylide. The chemical labelling exhibited a high selectivity towards f5C and allowed distinction from similar 5‐formyluridine. We realized a detection strategy based on the fluorescence signal of the cyclization product 4,5‐pyridin‐2‐amine‐cytidine paC, which exhibited a high quantum yield. The results clearly identified f5C with a limit of detection at 0.58 nM. This method altered the hydrogen bonding activities of f5C and modulated its reverse transcription signature in its sequencing profile. We showed that f5C can be detected from tRNA segments with a single‐base resolution. Taken together, this approach is a sensitive, antibody‐free, and applicable detection and sequencing method for f5C‐containing RNA.

  DOI：

  10.1002/anie.202210652

文献信息

• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR SYNTHESIS<br/>[FR] COMPOSÉS, COMPOSITIONS ET PROCÉDÉS DE SYNTHÈSE
  申请人：WAVE LIFE SCIENCES LTD

  公开号：WO2018237194A1

  公开（公告）日：2018-12-27

  The present disclosure, among other things, provides technologies for synthesis, including reagents and methods for stereoselective synthesis. In some embodiments, the present disclosure provides compounds useful as chiral auxiliaries. In some embodiments, the present disclosure provides reagents and methods for oligonucleotide synthesis. In some embodiments, the present disclosure provides reagents and methods for chirally controlled preparation of oligonucleotides. In some embodiments, technologies of the present disclosure are particularly useful for constructing challenging internucleotidic linkages, providing high yields and stereoselectivity.

  本公开内容提供了合成技术，包括用于立体选择性合成的试剂和方法。在某些实施例中，本公开内容提供了作为手性辅助剂有用的化合物。在某些实施例中，本公开内容提供了用于寡核苷酸合成的试剂和方法。在某些实施例中，本公开内容提供了用于手性控制寡核苷酸制备的试剂和方法。在某些实施例中，本公开内容的技术特别适用于构建具有挑战性的核苷酸间连接，提供高产率和立体选择性。
• [EN] NOVEL PHOSPHOROUS (V)-BASED REAGENTS, PROCESSES FOR THE PREPARATION THEREOF, AND THEIR USE IN MAKING STEREO-DEFINED ORGANOPHOSHOROUS (V) COMPOUNDS<br/>[FR] NOUVEAUX RÉACTIFS À BASE DE PHOSPHORE (V), LEURS PROCÉDÉS DE PRÉPARATION ET LEUR UTILISATION DANS LA FABRICATION DE COMPOSÉS ORGANOPHOSHOREUX (V) STÉRÉODÉFINIS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2019200273A1

  公开（公告）日：2019-10-17

  The present invention relates to novel phosphorous (V) (P(V)) reagents, methods for preparing thereof, and methods for preparing organophosphorous (V) compounds by using the novel reagents.

  本发明涉及新型磷（V）（P(V)）试剂，其制备方法以及利用这种新型试剂制备有机磷（V）化合物的方法。
• [EN] COMPOSITIONS AND METHODS FOR DELIVERY OF THERAPEUTIC AGENTS<br/>[FR] COMPOSITIONS ET PROCÉDÉS PERMETTANT D'ADMINISTRER DES AGENTS THÉRAPEUTIQUES
  申请人：MODERNATX INC

  公开号：WO2017099823A1

  公开（公告）日：2017-06-15

  This disclosure provides improved lipid-based compositions, including lipid nanoparticle compositions, and methods of use thereof for delivering agents in vivo including nucleic acids and proteins. These compositions are not subject to accelerated blood clearance and they have an improved toxicity profile in vivo.

  这项披露提供了改进的基于脂质的组合物，包括脂质纳米粒子组合物，以及它们用于体内传递药剂的方法，包括核酸和蛋白质。这些组合物不受加速血清清除的影响，并且它们在体内具有改进的毒性特性。
• [EN] TECHNOLOGIES USEFUL FOR OLIGONUCLEOTIDE PREPARATION<br/>[FR] TECHNOLOGIES UTILES POUR LA PRÉPARATION D'OLIGONUCLÉOTIDES
  申请人：WAVE LIFE SCIENCES LTD

  公开号：WO2020191252A1

  公开（公告）日：2020-09-24

  Among other things, the present disclosure provides technologies for oligonucleotide preparation, particularly chirally controlled oligonucleotide preparation, which technologies provide greatly improved crude purity and yield, and significantly reduce manufacturing costs.

  除其他事项外，本公开提供了寡核苷酸制备技术，特别是手性控制的寡核苷酸制备技术，这些技术大大提高了粗品纯度和产量，并显著降低了制造成本。
• [EN] OLIGONUCLEOTIDE COMPOSITIONS AND METHODS THEREOF<br/>[FR] COMPOSITIONS D'OLIGONUCLÉOTIDES ET PROCÉDÉS ASSOCIÉS
  申请人：WAVE LIFE SCIENCES LTD

  公开号：WO2019075357A1

  公开（公告）日：2019-04-18

  Among other things, the present disclosure provides technologies for altering splicing, particularly for increasing inclusion of exons in splicing products. In some embodiments, the present disclosure provides SMN2 oligonucleotides, compositions, and methods thereof. In some embodiments, the present disclosure provides chirally controlled SMN2 oligonucleotide compositions. In some embodiments, provided oligonucleotides and compositions can increase level of an exon 7-containing SMN2 splicing product and/or a gene product thereof. In some embodiments, the present disclosure provides methods for treatment of splicing-related conditions, disorders and diseases. In some embodiments, the present disclosure provides methods for treating SMN2-related conditions, disorders and diseases such as SMA (spinal muscular atrophy) and ALS (amyotrophic lateral sclerosis).

  本公开提供了用于改变剪接的技术，特别是用于增加剪接产物中外显子包含量的技术。在某些实施例中，本公开提供了SMN2寡核苷酸、组合物及其方法。在某些实施例中，本公开提供了立体控制的SMN2寡核苷酸组合物。在某些实施例中，所提供的寡核苷酸和组合物可以增加外显子7包含的SMN2剪接产物的水平和/或其基因产物的水平。在某些实施例中，本公开提供了用于治疗剪接相关疾病、疾病和疾病的方法。在某些实施例中，本公开提供了用于治疗SMN2相关疾病、疾病和疾病的方法，如脊髓性肌萎缩症（SMA）和肌萎缩侧索硬化（ALS）。