一种化学酶的途径,使得基纯的循环三级氨基
Colin J Dunsmore1, Reuben Carr, Toni Fleming
1School of Chemistry, University of Edinburgh, King's Buildings, West Mains Road, Edinburgh, EH9 3JJ, U.K.
Journal of the American Chemical Society
|February 16, 2006
概括
研究人员开发了一种单一的方法来脱血性三级胺. 这个过程使用一种进化的氨酸氧化酶和氨酸来有效地分离反体.
科学领域:
- 有机化学 有机化学
- 生物催化剂是一种生物催化剂.
- 酵素工程是什么意思 酵素工程
背景情况:
- 基拉尔三级胺是制药和精细化学品中至关重要的构建模块.
- 现有的分离反体的方法可能是低效的或需要恶劣的条件.
- 定向进化使得化学转换的高度特异性酶的发展成为可能.
研究的目的:
- 开发一种高效和可持续的方法来脱血血性性三级胺的脱血.
- 在单工艺中利用生物催化剂和化学还原剂的组合.
- 为了利用一种工程氨基氧化酶来进行反选择性氧化.
主要方法:
- 使用定向进化来获得一个enantioselective氨基氧化酶.
- 建立了一个单反应系统,将工程酶与氨酸结合起来.
- 种族性性三级胺受到反应条件的影响.
主要成果:
- 开发的单工艺成功实现了种族性性三级胺的脱血.
- 随机选择性氨基氧化酶表现出高效率和选择性.
- 氨基在组合系统中作为有效的减少剂.
结论:
- 导向进化衍生的氨氧化酶和氨基的组合为性氨酸脱血提供了一种新且高效的途径.
- 这一一策略为传统解决方案提供了一个可持续的替代方案.
- 这种工程酶有可能在不对称合成中得到更广泛的应用.
相关概念视频
Preparation of Amides
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Preparation of Amines: Alkylation of Ammonia and Amines
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Preparation of 1° Amines: Azide Synthesis
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
Amines to Amides: Acylation of Amines
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
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...


