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作为一个 (1) O2 敏感的链接剂,1,9-二氧化甲
Dumitru Arian1, Larisa Kovbasyuk, Andriy Mokhir
1Institute of Inorganic Chemistry, Ruprecht-Karls-University of Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
Journal of the American Chemical Society
|February 25, 2011
概括
研究人员开发了一种新的单片氧 (1O2) 敏感链接器,用于创建先进的分子工具. 这种连接器可以实现快速,高产量的反应,促进新探针和子化合物的开发.
科学领域:
- 有机化学 有机化学
- 生物化学 生物化学
- 分子生物学分子生物学
背景情况:
- 单片氧 (1O2) 在生物过程和光动力疗法中起着至关重要的作用.
- 开发精确的1O2检测和操纵工具对于生物研究和治疗应用至关重要.
研究的目的:
- 设计和合成一种基于9,10-dialkoxyanthracene结构的新型 (1) O (((2) 敏感链接剂.
- 开发一种化探针,用于在活哺乳动物细胞中监测 (1) O ((2)).
- 为了创建可见光激活的""寡氧化核酸,用于向的核酸输送.
主要方法:
- 合成含有 (1) O (((2) 敏感链接器的色胺基构件.
- 将链接器连接到各种分子碎片,包括核化物,光染料和胆固醇衍生物.
- 制备一个化探针,通过连接器连接四化素和四甲基胺.
- 用链接器在阻断链中构建""的寡氧化核酸.
主要成果:
- 敏感的链接器表现出快速和高收益的裂变在暴露于 (1) O 2 的情况下.
- 化探针显示灭的光,在链接器被 (1) O ((2) 裂开时恢复,与1 O 2度相关.
- 可见光激活的"子"寡氧化核酸被有效地解,释放具有高产量的活性链.
结论:
- 开发的 (1) O (((2) 敏感链接器是创建敏感探头和高效子化合物的通用构建模块.
- 化探针提供了一种可靠的方法,用于实时监测生物系统中的 (1) O ((2)).
- "中的"寡氧化核酸为光激活基因向和治疗应用提供了一个有前途的平台.
相关概念视频
01:12Cycloaddition Reactions: MO Requirements for Photochemical Activation
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
01:11Aryldiazonium Salts to Azo Dyes: Diazo Coupling
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
![[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2Ffiles%2Fmedia%2Fscience-education%2Fscience-education-thumbs%2F12417.jpg&w=3840&q=75)
01:16[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
02:04Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
03:00Preparation of Epoxides
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...