采用酒精脱的阿特罗普选择性生物催化剂
Gonzalo de Gonzalo1, Julia Carrión-González1, Juan M Coto-Cid1
1Department of Organic Chemistry, Universidad de Sevilla, Sevilla, Spain.
Methods in enzymology
|April 27, 2025
概括
这项研究介绍了一种生物催化方法,用于使用动态动力学分辨率 (DKR) 制造奇拉性异构化合物. 这种方法有效地产生了高纯度的价值的醇和氨酸基分子的化物.
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.
- 不对称的合成方法
背景情况:
- 轴性性异构化合物是有价值的合成标.
- 生物催化剂为人类选择性合成提供了一个可持续的途径.
- 动态动力学分辨率 (DKR) 能够实现赛米或性前体的转化.
研究的目的:
- 开发一种生物催化DKR,用于合成丰富的乙烯基化合物.
- 为了研究以醇和醇为基础的化物对人体选择性转化.
- 为了达到高产量和选择性,在合成奇拉性 heterobiaryl 酒精.
主要方法:
- 使用专门设计的基于醇和氨酸的化物作为基质.
- 使用商业可用的酒精脱酶 (ADHs) 进行反选择性降解.
- 应用溶剂工程用甲基 tert-butyl 以太或四基来增强对抗选择性.
主要成果:
- 通过DKR.获得高丰富的乙醇醇.
- 证明了ADHs的反异性合成能力.
- 在大多数基板上获得了优异的产量和反体过量 (ee > 90%).
- 通过溶剂工程改善了低EE值 (<90%).
结论:
- 生物催化DKR是一种有效的策略,用于合成轴性性异构化合物.
- 基板内的非共价易斯相互作用促进了活化.
- 这种方法可以获得具有高光学纯度的多种类型的异构醇.
相关概念视频
Acid-Catalyzed Dehydration of Alcohols to Alkenes
18.9K
In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
18.9K
Aldehydes and Ketones with Alcohols: Hemiacetal Formation
5.5K
Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
5.5K
Hydroboration-Oxidation of Alkenes
7.6K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
7.6K
Preparation of Alcohols via Addition Reactions
6.1K
Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
6.1K
Alcohols from Carbonyl Compounds: Reduction
10.1K
Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat...
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat...
10.1K
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
3.7K
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...
3.7K


