阿尔多酶衍生3-氧基的生物催化转胺
Mathias Pickl1,2, Markus Ebner2, Samantha Gittings3
1Department of Chemical Biology Instituto de Química Avanzada de Cataluña (IQAC-CSIC) Jordi Girona 18-26 08034 Barcelona Spain.
Advanced synthesis & catalysis
|March 22, 2024
概括
这项研究提出了一种新的多酶方法,用于从简单化学物质中合成丰富的1,3-氨基醇. 该过程避免了复杂的保护策略,产生具有高立体选择性的产品.
科学领域:
- 生物催化剂是一种生物催化剂.
- 有机合成 有机合成
- 立体选择性合成 立体选择性合成
背景情况:
- 光学纯氨基醇是有价值的,但很难用传统方法合成.
- 现有的合成路线往往需要复杂的保护和降低保护步骤,增加效率.
研究的目的:
- 开发一种简化,多酶的方法,以高效合成富含1,3-氨基醇.
- 为了规避在氨基醇合成中需要精心设计的保护策略.
主要方法:
- 使用I型阿尔多酶构建碳骨干,创建一个丰富的阿尔多基因.
- 使用194个转氨酶 (TA) 的图书馆进行酶转氨基化,以引入氨基组.
- 选了使用各种核友和电友生成的多种 aldol 产品.
主要成果:
- 成功合成了多达三个奇拉中心的1,3-氨基醇.
- 在最终产品中实现了高 diastereoselectivity (高达>97%) 的作用.
- 通过选择适当的TA,证明了对 (R) - 和 (S) - 选择性异构体的获取.
结论:
- 提出的多酶方法提供了一个高效和多功能途径,以光学纯净的1,3-氨基醇.
- 这种生物催化方法通过避免保护组操纵来简化合成.
- 该方法可以从商品化学品中获取多样化,高度立体定义的氨基醇结构.
相关概念视频
Base-Catalyzed Aldol Addition Reaction
3.3K
As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
3.3K
Acid-Catalyzed Aldol Addition Reaction
2.5K
The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
2.5K
Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction
2.2K
The reaction between two different carbonyl compounds comprising α hydrogen in the presence of a strong base like lithium diisopropylamide (LDA) to form a crossed aldol product is known as a directed aldol reaction. The directed aldol reaction is depicted in Figure 1.
2.2K
Aldol Condensation with β-Diesters: Knoevenagel Condensation
3.0K
The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.
3.0K
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
4.1K
Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...
The carbonyl center is...
4.1K
Crossed Aldol Reaction Using Weak Bases
2.1K
This lesson deals with the crossed aldol reaction using weak bases. The self-condensation of an aldehyde having α hydrogen is prevented by adding it slowly to a mixture of formaldehyde and weak bases like hydroxide and alkoxide. Upon slow addition of the aldehyde, the base deprotonates the α carbon of the aldehyde to form the corresponding enolate. The enolate subsequently attacks the formaldehyde to form a single crossed product. Figure 1 depicts the aforementioned reaction.
2.1K


