1-(5-(azidomethyl)-2-nitrophenyl)ethan-1-ol | 1241387-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(5-(azidomethyl)-2-nitrophenyl)ethan-1-ol
• 英文别名: 1-[5-(Azidomethyl)-2-nitrophenyl]ethanol
• CAS: 1241387-87-0
• 化学式: C₉H₁₀N₄O₃
• 分子量: 222.203
• InChiKey: DQVDMIZIMIDWEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(5-(azidomethyl)-2-nitrophenyl)ethan-1-ol 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成 1-[5-{N-(5-bromopentanoyl)aminomethyl}-2-nitrophenyl]ethanol
  参考文献：
  名称：

  一种“捕获和释放”策略，通过应变促进炔-叠氮化物环加成和光裂解的组合，无HPLC纯化合成寡核苷酸

  摘要：

  描述了一种纯化策略，用于纯化在自动DNA / RNA合成仪上通过固相合成合成的寡核苷酸（ON）。通过将光可裂解的叠氮基连接基连接为ON合成中的最后一个亚磷酰胺单元，只有所需的全长序列被“捕获”在具有氮杂二甲氧基环辛炔（DIBAC）衍生物的可控孔玻璃（CPG）树脂上。洗涤所得的CPG树脂以除去所有未结合的物质，随后的光辐照使纯ON得以“释放”，而对天然ON结构或固相ON合成中的化学试剂没有任何化学修饰。

  DOI：

  10.1016/j.bmc.2017.09.014
• 作为产物：
  描述：

  5-甲基-2-硝基苯甲酸 在 盐酸 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 sodium azide 、 水 、 magnesium 、 过氧化苯甲酰 作用下， 以 1,4-二氧六环 、 四氯化碳 、 水 、 丙酮 为溶剂， 反应 0.5h， 生成 1-(5-(azidomethyl)-2-nitrophenyl)ethan-1-ol
  参考文献：
  名称：

  Cleavable Biotin Probes for Labeling of Biomolecules via Azide−Alkyne Cycloaddition

  摘要：

  The azide-alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling experiments, e.g., in proteomic studies involving affinity purification and mass spectrometry, it is convenient to use cleavable probes that allow release of labeled biomolecules under mild conditions. Five cleavable biotin probes are described for use in labeling of proteins and other biomolecules via azide-alkyne cycloaddition. Subsequent to conjugation with metabolically labeled protein, these probes are subject to cleavage with either 50 mM Na2S2O4, 2% HOCH2CH2SH, 10% HCO2H, 95% CF3CO2H, or irradiation at 365 nm. Most strikingly, a probe constructed around a dialkoxydiphenylsilane (DADPS) linker was found to be cleaved efficiently when treated with 10% HCO2H for 0.5 h. A model green fluorescent protein was used to demonstrate that the DADPS probe undergoes highly selective conjugation and leaves a small (143 Da) mass tag on the labeled protein after cleavage. These features make the DADPS probe especially attractive for use in biomolecular labeling and proteomic studies.

  DOI：

  10.1021/ja1083909

文献信息

• Convenient RNA Synthesis Using a Phosphoramidite Possessing a Biotinylated Photocleavable Group
  作者：Kota Tomaya、Mayumi Takahashi、Noriaki Minakawa、Akira Matsuda

  DOI：10.1021/ol101489v

  日期：2010.9.3

  A convenient RNA synthesis using a biotin streptavidin interaction and a photocleavable protecting group is described. The biotinylated photocleavable group was introduced at the 2'-position of the uridine derivative. Using the phosphoramidite 12, we attempted the synthesis of a 21mer RNA, which is pure enough to show potent RNAi activity compared with a conventionally prepared and HPLC-purified 21mer RNA with the same sequence.
• A METHOD OF IDENTIFYING OR PRODUCING AN APTAMER
  申请人：Tolle, Fabian

  公开号：EP3052653A1

  公开（公告）日：2016-08-10
• [EN] A METHOD OF IDENTIFYING OR PRODUCING AN APTAMER<br/>[FR] PROCÉDÉ D'IDENTIFICATION OU DE PRODUCTION D'UN APTAMÈRE
  申请人：TOLLE FABIAN

  公开号：WO2015049356A1

  公开（公告）日：2015-04-09

  The invention relates to amethod of identifying or producing an aptamer,and a reagent comprising a nucleic acid ligand capable of binding a target sample, wherein the nucleic acid ligand comprises at least one nucleobase modified to contain an azide-alkyne chemical group.
• [EN] METHOD AND COMPOUND<br/>[FR] PROCÉDÉ ET COMPOSÉ
  申请人：[en]ATDBIO LIMITED

  公开号：WO2023180237A1

  公开（公告）日：2023-09-28

  Provided herein is a method for modifying a polynucleotide or an analogue or derivative thereof, comprising reacting the polynucleotide or analogue or derivative thereof with a compound of formula (I), wherein RH, L1, Ⓛ, R, n and RPare as defined herein. Also provided are associated methods for purifying a polynucleotide or analogue or derivative thereof, uses of a compound of formula (I), and such compounds per se.