TCO-Acetic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: TCO-Acetic acid
• 英文别名: 2-[(4E)-cyclooct-4-en-1-yl]oxyacetic acid
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: ZVJNYABHPQDPNJ-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  TCO-Acetic acid 、 2,4,5-三氯苯酚 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以57%的产率得到
  参考文献：
  名称：

  Bio-orthogonal chemistry enables solid phase synthesis and HPLC and gel-free purification of long RNA oligonucleotides

  摘要：

  一种基于生物正交化学的策略使得长RNA寡核苷酸的固相合成和纯化成为可能。

  DOI：

  10.1039/d1cc00096a
• 作为产物：
  描述：

  5-hydroxy-1-cyclooctene 在 苯甲酸甲酯 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 mineral oil 为溶剂， 反应 7.0h， 生成 TCO-Acetic acid
  参考文献：
  名称：

  反式环辛烯四嗪连接制备小分子微阵列及其在溴结构域蛋白-蛋白质相互作用抑制剂高通量筛选中的应用

  摘要：

  快速高效：通过使用已知最快的生物正交反应，将反式环辛烯（TCO）修饰的小分子文库固定在四嗪功能化的载玻片上。针对各种人类溴结构域筛选了所得的小分子微阵列，以鉴定蛋白质-蛋白质相互作用抑制剂。

  DOI：

  10.1002/anie.201307803

文献信息

• TETRAZINE-BASED BIO-ORTHOGONAL COUPLING REAGENTS AND METHODS
  申请人：Fox Joseph Michael

  公开号：US20090023916A1

  公开（公告）日：2009-01-22

  Coupling reactions, suitable for use in organic or aqueous media, are performed by contacting a 1,2,4,5-tetrazine with a dienophile. The dienophile may be covalently bonded to a protein, and the coupling reaction may be performed in biological media such as those containing cells or cell lysates. The reactions may be performed in the presence of primary amines, thiols, acetylenes, azides, phosphines, and products of Staudinger and/or Sharpless-Huisgen reactions Novel 3-substituted cyclopropene compounds and trans-cyclooctenes are exemplary dienophiles for these reactions.

  耦合反应，适用于有机或水性介质，通过将1,2,4,5-四唑与二烯丙烯发生反应来进行。二烯丙烯可能与蛋白质共价结合，耦合反应可在含有细胞或细胞裂解产物的生物介质中进行。这些反应可在存在主要胺基、硫醇、乙炔、叠氮化物、膦化合物以及Staudinger和/或Sharpless-Huisgen反应产物的情况下进行。新颖的3-取代环丙烯化合物和反式-环辛烯是这些反应的优秀二烯丙烯。
• PRETARGETING KIT, METHOD AND AGENTS USED THEREIN
  申请人：Lub Johan

  公开号：US20130189184A1

  公开（公告）日：2013-07-25

  Described is a pretargeting method, and related kits, for targeted medical imaging and/or therapeutics, wherein use is made of abiotic reactive chemical groups that exhibit bio-orthogonal reactivity towards each other. The invention involves the use of [4+2] inverse electron demand (retro) Diels-Alder chemistry in providing the coupling between a Pre-targeting Probe and an Effector Probe. To this end one of these probes comprises an electron-deficient tetrazine or other suitable diene, and the other an E-cyclooctene which has one or more axial substituents.

  描述了一种预靶向方法及相关试剂盒，用于靶向医学成像和/或治疗，其中利用表现出生物正交反应性的无机反应性化学基团。该发明涉及使用[4+2]逆电子需求（反）Diels-Alder化学在预靶向探针和效应探针之间提供偶联。为此，其中一种探针包括富电子缺陷的四唑或其他适当的双烯，另一种是具有一个或多个轴取代基的E-环辛烯。
• AGENTS FOR CLEARING BIOMOLECULES FROM CIRCULATION
  申请人：Rossin Raffaella

  公开号：US20130272959A1

  公开（公告）日：2013-10-17

  Described is a method, and a combination of agents for used therein, by which an agent administered to a subject can be rapidly cleared from circulation. This is achieved by providing an Administration Agent (e.g. a probe for pretargeting) with a reactive group and providing a Clearing Agent with another reactive group, said reactive groups forming a bio-orthogonally reactive pair. Preferably, the reactive pair comprises a cyclooctene or cyclooctyn as one reactant, and a diene as the other reactant. The method and combination can be used for the removal of any bindable molecule from circulation, such as an excess of a pre-targeting probe in the course of a pre-targeting method, a targeting or imaging agent delivered, or the removal of any biomolecule already present in circulation.

  描述了一种方法，以及其中使用的一组药剂组合，通过该方法，可以迅速清除给予受试者的药剂在循环中的存在。这是通过提供具有反应基团的给药剂（例如，用于预先靶向的探针）和提供具有另一种反应基团的清除剂来实现的，所述反应基团形成生物正交反应对。最好，反应对包括环辛烯或环辛炔作为一种反应物，二烯作为另一种反应物。该方法和组合可用于从循环中去除任何可结合分子，例如，在预先靶向方法中清除探针的过量，传递的靶向或成像剂，或已存在于循环中的任何生物分子的清除。
• Bio-orthogonal chemistry-based method for fluorescent labelling of ribosomal RNA in live mammalian cells
  作者：K. Wu、M. He、I. Khan、P. N. Asare Okai、Q. Lin、G. Fuchs、M. Royzen

  DOI：10.1039/c9cc05346h

  日期：——

  chemistry-based approach for fluorescent labelling of ribosomal RNA is described. It involves an adenosine analogue modified with trans-cyclooctene and masked 5′-phosphate group using aryl phosphoramidate. The incorporation into rRNA has been confirmed using agarose gel electrophoresis, as well as a highly sensitive UHPLC-MS/MS method. Fluorescent labelling of rRNA has been achieved in live HeLa cells via an inverse

  描述了一种基于生物正交化学的核糖体RNA荧光标记方法。它涉及用反式-环辛烯修饰的腺苷类似物，并使用氨基磷酸氨基酯掩蔽的5'-磷酸基团。使用琼脂糖凝胶电泳以及高灵敏度的UHPLC-MS / MS方法已证实将其掺入rRNA中。rRNA的荧光标记已经在活HeLa细胞中通过逆电子需求Diels-Alder反应以及与俄勒冈绿色荧光团偶联的四嗪实现。本交流描述了逐步开发方法，该方法导致了探头的开发和表征。结果证明了开发未来荧光探针以研究核酸的生物化学的新策略。
• A Photochemical Synthesis of Functionalized <i>trans</i>-Cyclooctenes Driven by Metal Complexation
  作者：Maksim Royzen、Glenn P. A. Yap、Joseph M. Fox

  DOI：10.1021/ja8001919

  日期：2008.3.1

  Described is a scalable procedure for driving photochemical sytheses of trans-cyclooctene derivatives through metal complexation. During photoirradiation, reaction mixtures are continuously pumped through a column of a AgNO(3)-impregnated silica gel. The trans-cyclooctene derivative is selectively retained by the AgNO3-impregnated silica, but the cis-isomer elutes from the column back to the reaction flask, where it is photoisomerized and recirculated through the column. The method provides access to a range of usefully functionalized derivatives of trans-cyclooctene, including a derivative of 5-aza-trans-cyclooctene that underwent transannular cyclization upon treatment with bromine. The alkene stereochemistry is transferred with high fidelity to the hexahydropyrrolizine framework in the transannular cyclization.