2,5-dioxopyrrolidin-1-yl 3-{[2-(1-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-3,6,9,12-tetraoxapentadecan-15-amido)ethyl]disulfanyl}propanoate | 1260247-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 2,5-dioxopyrrolidin-1-yl 3-{[2-(1-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-3,6,9,12-tetraoxapentadecan-15-amido)ethyl]disulfanyl}propanoate
• 英文别名: NHS-SS-PEG₄-biotin；Biot-Peg4-SS-CONHS；Biotin-PEG4-S-S-NHS；(2,5-dioxopyrrolidin-1-yl) 3-[2-[3-[2-[2-[2-[2-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]propanoylamino]ethyldisulfanyl]propanoate
• CAS: 1260247-51-5
• 化学式: C₃₀H₄₉N₅O₁₁S₃
• 分子量: 751.944
• InChiKey: QEVJWOMRMWJABZ-BOSRLCDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  49
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  276
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2,5-dioxopyrrolidin-1-yl 3-{[2-(1-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-3,6,9,12-tetraoxapentadecan-15-amido)ethyl]disulfanyl}propanoate 、 tert-butyl 5-amino-2-(methylamino)benzoate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83%的产率得到tert-butyl 5-(3-{[2-(1-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-3,6,9,12-tetraoxapentadecan-15-amido)ethyl]disulfanyl}propanamido)-2-(methylamino)benzoate
  参考文献：
  名称：

  Biotin-conjugated N-methylisatoic anhydride: a chemical tool for nucleic acid separation by selective 2′-hydroxyl acylation of RNA

  摘要：

  一种异烟酰亚胺衍生物，带有生物素和二硫化物连接剂，专门设计用于通过RNA的选择性2'-羟基酰化分离核酸。

  DOI：

  10.1039/c4cc01134a

文献信息

• A Color‐Shifting Near‐Infrared Fluorescent Aptamer–Fluorophore Module for Live‐Cell RNA Imaging
  作者：Jingye Zhang、Lu Wang、Andres Jäschke、Murat Sunbul

  DOI：10.1002/anie.202107250

  日期：2021.9.20

  Fluorescent light-up RNA aptamers (FLAPs) have become promising tools for visualizing RNAs in living cells. Specific binding of FLAPs to their non-fluorescent cognate ligands results in a dramatic fluorescence increase, thereby allowing RNA imaging. Here, we present a color-shifting aptamer-fluorophore system, where the free dye is cyan fluorescent and the aptamer-dye complex is near-infrared (NIR)

  荧光点亮 RNA 适配体 (FLAP) 已成为可视化活细胞中 RNA 的有前途的工具。FLAPs 与其非荧光同源配体的特异性结合导致荧光显着增加，从而允许 RNA 成像。在这里，我们提出了一种变色适体-荧光团系统，其中游离染料为青色荧光，而适体-染料复合物为近红外 (NIR) 荧光。与其他报道的 FLAPs 不同，该系统能够实现比率 RNA 成像。为了设计变色系统，我们合成了一系列环境敏感的苯并吡喃-香豆素杂化荧光团，它们在青色荧光螺环形式和 NIR 荧光两性离子形式之间处于平衡状态。作为 RNA 标签，我们进化出 38 个核苷酸的适体，以纳摩尔亲和力选择性结合两性离子形式。
• MODIFIED NUCLEOTIDES METHODS AND KITS
  申请人：Etienne Christopher L.

  公开号：US20120252691A1

  公开（公告）日：2012-10-04

  Modified nucleotides, and methods to modify nucleotides with a moiety or label, such as biotin, that permits their detection and results in a modified nucleotide, and methods of use of the modified nucleotide in quantitative and qualitative assays.

  修饰核苷酸及其修饰方法，使用含有生物素等标记的基团修饰核苷酸，使其能够被检测，从而得到修饰后的核苷酸，并且使用修饰后的核苷酸进行定量和定性分析的方法。
• Modified Nucleotides Methods and Kits
  申请人：Pierce Biotechnology, Inc.

  公开号：EP2669291A1

  公开（公告）日：2013-12-04

  Modified nucleotides, and methods to modify nucleotides with a moiety or label, such as biotin, that permits their detection and results in a modified nucleotide, and methods of use of the modified nucleotide in quantitative and qualitative assays. The modified nucleotide compound having the structure (I): (P1)(P2)-Nucleoside(Nus)-Connecting Group (Alk)-Linking Group (Lnk)-Observable Label (Obs) (I).

  修改核苷酸，以及使用可以检测它们并导致修改核苷酸的基团或标签（例如生物素）来修改核苷酸的方法，以及在定量和定性分析中使用修改核苷酸的方法。具有结构（I）的修改核苷酸化合物：（P1）（P2）-核苷（Nus）-连接基团（Alk）-连接基团（Lnk）-可观察标签（Obs）（I）。
• Cleavable Biotin Probes for Labeling of Biomolecules via Azide−Alkyne Cycloaddition
  作者：Janek Szychowski、Alborz Mahdavi、Jennifer J. L. Hodas、John D. Bagert、John T. Ngo、Peter Landgraf、Daniela C. Dieterich、Erin M. Schuman、David A. Tirrell

  DOI：10.1021/ja1083909

  日期：2010.12.29

  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.
• US8536323B2
  申请人：——

  公开号：US8536323B2

  公开（公告）日：2013-09-17