快速的化学选择性生物结合通过氧化合的anilines和aminophenols
Christopher R Behrens1, Jacob M Hooker, Allie C Obermeyer
1Department of Chemistry, University of California, Berkeley, California 94720-1460, USA.
Journal of the American Chemical Society
|September 17, 2011
概括
一种新的蛋白质生物结合方法使用aniline和o-aminophenols进行快速,高效的分子附着. 这种氧化环收缩反应与各种蛋白质修饰和基质相容.
科学领域:
- 生物结合化学 生物结合化学
- 蛋白质工程是指蛋白质工程.
- 有机合成 有机合成
背景情况:
- 蛋白质修饰对于开发诊断和治疗方法至关重要.
- 现有的生物结合方法通常需要恶劣的条件或缺乏效率.
- 需要快速,多功能和生物相容的蛋白质标签技术.
研究的目的:
- 开发一种高效和快速的蛋白质生物结合方法.
- 描述反应机制及其产物.
- 为了证明该方法在蛋白质修饰中的广泛适用性.
主要方法:
- 在水性缓冲体中由 sodium periodate 催化的 o-aminophenols 中添加anilines (pH 6.5).
- 使用X射线晶体学对主要产品的表征.
- 证明与蛋白质基质的兼容性,包括通过珀停止密码子抑制修改的病毒囊.
- 病毒体的顺序修改,首先向氨酸残留物,然后向氨酸组.
主要成果:
- 在温和的水性条件下,反应在2-5分钟内实现高转化.
- 射线晶体学揭示了一个前所未有的氧化环收缩机制.
- 该方法成功地将小分子,聚合物链和与蛋白质连接起来.
- 与硫醇修饰和顺序标记策略的证明兼容性.
结论:
- 已经建立了一个新的,快速和高效的蛋白质生物结合策略.
- 该方法独特的氧化环收缩机制为生物结合提供了新的可能性.
- 这种多功能技术适用于蛋白质标记和功能化的各种应用.
相关概念视频
Aryldiazonium 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.
Phase II Conjugation Reactions: Overview
Conjugation, a key component of phase II biotransformation reactions, is a vital process in drug detoxification. It involves transferring endogenous substances like glucuronic acid, sulfate, and glycine to drugs or their metabolites formed in phase I reactions. These conjugation reactions, often catalyzed by specific enzymes, transform potentially harmful metabolites into inactive, water-soluble forms easily excreted in urine or bile. By enhancing polarity and eliminating pharmacological...
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
Preparation of Amines: Reduction of Oximes and Nitro Compounds
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Oxidation 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.


