4-(1-fluoro-cyclooct-2-ynylmethyl)benzoic acid | 886209-46-7

• 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: 4-(1-fluoro-cyclooct-2-ynylmethyl)benzoic acid
• 英文别名: MOFO；4-[(1-fluorocyclooct-2-yn-1-yl)methyl]benzoic acid
• CAS: 886209-46-7
• 化学式: C₁₆H₁₇FO₂
• 分子量: 260.308
• InChiKey: BPIOJHYGHPDOFG-UHFFFAOYSA-N

物化性质

• 熔点：
  132.0-132.5 °C (decomp)
• 沸点：
  400.7±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1-fluoro-cyclooct-2-ynylmethyl)benzoic acid 在 三氟乙酸五氟苯酯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  Fluorophore Targeting to Cellular Proteins via Enzyme-Mediated Azide Ligation and Strain-Promoted Cycloaddition

  摘要：

  Methods for targeting of small molecules to cellular proteins can allow imaging with fluorophores that are smaller, brighter, and more photostable than fluorescent proteins. Previously, we reported targeting of the blue fluorophore coumarin to cellular proteins fused to a 13-amino acid recognition sequence (LAP), catalyzed by a mutant of the Escherichia coli enzyme lipoic acid ligase (LplA). Here, we extend LplA-based labeling to green- and red-emitting fluorophores by employing a two-step targeting scheme. First, we found that the W37I mutant of LplA catalyzes site-specific ligation of 10-azidodecanoic acid to LAP in cells, in nearly quantitative yield after 30 min. Second, we evaluated a panel of five different cyclooctyne structures and found that fluorophore conjugates to aza-dibenzocyclooctyne (ADIBO) gave the highest and most specific derivatization of azide-conjugated LAP in cells. However, for targeting of hydrophobic fluorophores such as ATTO 647N, the hydrophobicity of ADIBO was detrimental, and superior targeting was achieved by conjugation to the less hydrophobic monofluorinated cyclooctyne (MOFO). Our optimized two-step enzymatic/chemical labeling scheme was used to tag and image a variety of LAP fusion proteins in multiple mammalian cell lines with diverse fluorophores including fluorescein, rhodamine, Alexa Fluor 568, ATTO 647N, and ATTO 655.

  DOI：

  10.1021/ja208090p
• 作为产物：
  描述：

  4-(1-fluoro-2-trifluoromethanesulfonyloxy-cyclooct-2-enylmethyl)-benzoic acid methyl ester 在 水 、 lithium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正庚烷 、 乙基苯 为溶剂， 反应 3.0h， 生成 4-(1-fluoro-cyclooct-2-ynylmethyl)benzoic acid
  参考文献：
  名称：

  Compositions and methods for modification of biomolecules

  摘要：

  本发明提供了改性的环炔化合物；以及使用这些化合物在生理条件下进行生物分子修饰的方法。本发明特点是一种可以在生理条件下进行的环加成反应。一般来说，该发明涉及将改性的环炔与目标生物分子上的叠氮基团反应，生成共价修饰的生物分子。该反应的选择性和与水环境的兼容性使其适用于体内（例如，细胞表面或细胞内）和体外（例如，合成肽类和其他聚合物，生产修饰的（例如，标记的）氨基酸）的应用。

  公开号：

  US09260371B2

文献信息

• Methods and compositions for protein labeling using lipoic acid ligases
  申请人：Ting Alice Y.

  公开号：US09284541B2

  公开（公告）日：2016-03-15

  The present disclosure provides compositions and methods of use thereof for labeling peptide and proteins in vitro or in vivo. The methods described herein employ lipoic acid ligase or mutants thereof, and lipoic acid analogs (e.g., lipoic acid analogs comprising a resorufin moiety) recognized by lipoic acid ligase and lipoic acid ligase mutants. Also provided herein is a method of imaging protein-protein interaction via a reaction mediated by lipoic acid ligase.

  本公开提供了用于在体外或体内标记肽和蛋白质的组成物及其使用方法。所述方法采用丙酸酸化酶或其突变体，以及丙酸酸化酶和丙酸酸化酶突变体所识别的丙酸类似物（例如，包含resorufin部分的丙酸类似物）。此外，还提供了一种通过丙酸酸化酶介导的反应来成像蛋白质-蛋白质相互作用的方法。
• Copper-free click chemistry for the in situ crosslinking of photodegradable star polymers
  作者：Jeremiah A. Johnson、Jeremy M. Baskin、Carolyn R. Bertozzi、Jeffrey T. Koberstein、Nicholas J. Turro

  DOI：10.1039/b803043j

  日期：——

  Bifunctional, fluorinated cyclooctynes were used for the in situ “click” crosslinking of azide-terminated photodegradable star polymers, yielding photodegradable polymeric model networks with well-defined structures and tunable gelation times.

  双官能氟化环辛炔被用于叠氮封端光降解星型聚合物的原位 "点击 "交联，产生了具有明确结构和可调凝胶时间的光降解聚合物模型网络。
• COMPOSITIONS AND METHODS FOR MODIFICATION OF BIOMOLECULES
  申请人：BERTOZZI CAROLYN RUTH

  公开号：US20090068738A1

  公开（公告）日：2009-03-12

  The present invention provides modified cycloalkyne compounds; and method of use of such compounds in modifying biomolecules. The present invention features a cycloaddition reaction that can be carried out under physiological conditions. In general, the invention involves reacting a modified cycloalkyne with an azide moiety on a target biomolecule, generating a covalently modified biomolecule. The selectivity of the reaction and its compatibility with aqueous environments provide for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).

  本发明提供了改性的环烷炔化合物；以及使用这些化合物在修饰生物分子方面的方法。本发明特点是可以在生理条件下进行环加成反应。通常，本发明涉及将改性的环烷炔与目标生物分子上的偶氮基团反应，生成共价修饰的生物分子。该反应的选择性及其与水性环境的兼容性使其适用于体内（例如，细胞表面或细胞内）和体外（例如，合成肽和其他聚合物，生产改性（例如，标记）氨基酸）的应用。
• PROBE INCORPORATION MEDIATED BY ENZYMES
  申请人：Massachusetts Institute of Technology

  公开号：US20150125904A1

  公开（公告）日：2015-05-07

  Compositions (e.g., lipoic acid ligase polypeptides and lipoic acid analogs) and uses thereof in the Probe Incorporation Mediated By Enzymes (PRIME) methods both in vitro and in vivo. Also described herein are kits for performing the PRIME method and vectors/kits for expressing the lipoic acid ligases.

  本文描述了在体内外中使用组合物（例如，硫辛酸连接酶多肽和硫辛酸类似物）及其在酶媒介的探针合成（PRIME）方法中的用途。还描述了用于执行PRIME方法的工具包以及用于表达硫辛酸连接酶的载体/工具包。
• Compositions and Methods for Modification of Biomolecules
  申请人：The Regents of the University of California

  公开号：US20130344527A1

  公开（公告）日：2013-12-26

  The present invention provides modified cycloalkyne compounds; and method of use of such compounds in modifying biomolecules. The present invention features a cycloaddition reaction that can be carried out under physiological conditions. In general, the invention involves reacting a modified cycloalkyne with an azide moiety on a target biomolecule, generating a covalently modified biomolecule. The selectivity of the reaction and its compatibility with aqueous environments provide for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).

  本发明提供了改性环烷炔化合物；以及使用这种化合物修饰生物分子的方法。本发明特点是可以在生理条件下进行环加成反应。一般来说，本发明涉及将改性环烷炔与目标生物分子上的叠氮基团反应，生成共价修饰的生物分子。反应的选择性及其与水性环境的兼容性使其适用于体内（例如，细胞表面或细胞内）和体外（例如，合成肽和其他聚合物，生产改性（例如，标记）氨基酸）。