在水中协同进行的一生物催化氧化和维蒂格反应
Alice J C Wahart1, Liam N D Beardmore1, Robert A Field2
1School of Chemical and Physical Sciences and Centre for Glycoscience, Keele University, Keele, Staffordshire ST5 5BG, U.K.
Organic letters
|July 30, 2024
概括
这项研究引入了一种新的生物催化方法,用于在水中产生化物,从而使多种烯合成的单维蒂格反应成为可能. 工程酶对各种功能组具有广泛的基质耐受性.
科学领域:
- 生物催化和有机合成
- 酶工程是什么? 酶工程是什么?
背景情况:
- 传统的维蒂格反应通常需要恶劣的条件和有机溶剂.
- 在绿色化学中,开发可持续和高效的化物生成和后续反应方法至关重要.
研究的目的:
- 开发一种单生物催化方法,用于在水性介质中产生化物和维蒂格反应.
- 为了证明复合胆氧化酶突变体对酒精氧化物的基质耐受性.
- 为了在温和,环保的条件下实现各种烯产品的高效合成.
主要方法:
- 使用一种重组胆氧化酶突变体,用于功能性非性初级酒精的生物催化氧化.
- 在水溶液中使用稳定酸盐进行了单维蒂格反应.
- 为毫克级合成优化反应条件.
主要成果:
- 工程化胆氧化酶表现出广泛的基质耐受性,可以接受含化物,化物,亚化物,S-甲基和基基基的酒精.
- 通过水中的单维蒂格反应成功生成了多种烯产物.
- 在毫克尺度上证明了该方法的实用性.
结论:
- 生物催化性化物生成,然后在水中进行单维蒂格反应是一个可行的和可持续的合成策略.
- 工程化胆氧化酶是一种强大的催化剂,用于氧化广泛的功能性酒精.
- 这种方法为烯合成提供了一个更绿色的替代方案,最大限度地减少有机溶剂的使用和反应步骤.
相关概念视频
01:14Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
3.4K
The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
3.4K
01:19Aldehydes and Ketones to Alkenes: Wittig Reaction Overview
7.6K
The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
7.6K
02:15Preparation of Alcohols via Addition Reactions
6.2K
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...
6.2K
02:04Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
5.7K
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.
5.7K
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
10.0K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.0K
02:37Oxidation of Alcohols
12.9K
In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
The process of oxidation in a chemical reaction is observed in any of the three forms:
12.9K