氧化胺基合成和N端α-氨基基团合在水性介质中的
Wing-Kei Chan1, Chi-Ming Ho, Man-Kin Wong
1Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, China.
Journal of the American Chemical Society
|November 16, 2006
概括
一种新型的催化方法有效地利用催化剂和水中的氧化剂从和胺中合成胺. 这种方法使轻度的N端与各种基因结合成为可能.
科学领域:
- 有机化学 有机化学
- 催化剂是一种催化剂.
- 生物化学 生物化学
背景情况:
- 胺基键的形成在有机合成和化学中至关重要.
- 开发高效和温和的合成方法是一个持续的挑战.
研究的目的:
- 开发一种用于胺合成的新氧化方法.
- 为了利用一个催化剂,有效地形成胺基.
- 为了在温和的条件下使结合成为可能.
主要方法:
- 和胺的氧化合.
- 使用[Mn(2,6-Cl2TPP) Cl]作为催化剂.
- 在水性介质中使用氧子/H2O2作为氧化剂.
主要成果:
- 实现了高胺产量 (高达96%).
- 成功结合未受保护的N端α-氨基基组.
- 与阿里尔,阿利法和内部基具有证明的兼容性.
结论:
- 已经建立了一种新的,高效和温和的氨基酸合成和结合的方法.
- 开发的催化系统为有机和化学提供了宝贵的工具.
- 水态反应条件突出显示了绿色合成方法的潜力.
相关概念视频
Organic Compounds
All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
Water: A Bronsted-Lowry Acid and Base
The reaction between a Brønsted-Lowry acid and water is called acid ionization. For example, when hydrogen fluoride dissolves in water and ionizes, protons are transferred from hydrogen fluoride molecules to water molecules, yielding hydronium ions and fluoride ions:
Nucleophilic Substitution Reactions
Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
Acid Halides to Esters: Alcoholysis
Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Preparation of 1° Amines: Gabriel Synthesis
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...


