通过工程性酒精氧化酶有效合成1,4-环二氧化碳化物
Yaqi Cheng1, Wei Song1, Xiulai Chen2
1School of Life Sciences and Health Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, 214122, China.
Bioresources and bioprocessing
|April 22, 2024
概括
研究人员设计了一种酒精氧化酶 (AOX) 酶,从1,4-cyclohexanedimethanol (CHDM) 中有效地产生1,4-cyclohexanedicarboxaldehyde (CHDA). 这种增强的酶变体显示了工业CHDA生产的巨大潜力.
科学领域:
- 生物催化剂是一种生物催化剂.
- 酶工程是什么? 酶工程是什么?
- 有机合成 有机合成
背景情况:
- 黄氨酸二核酸 (FAD) 依存的酒精氧化酶 (AOX) 催化初级酒精氧化.
- 化物转移中的高能障碍限制了野生型AOX的催化效率.
- 1,4-环二甲 (CHDA) 是螺旋化合物的关键中间体.
研究的目的:
- 从1,4-环二甲醇 (CHDM) 改进生产CHDA的AOX工程.
- 阐明AcCO催化初级酒精氧化的机制,并确定速度限制的步骤.
- 通过降低化物转移的能量障碍来提高催化效率.
主要方法:
- 对Arthrobacter cholorphenolicus酒精氧化酶 (AcCO) 结构和催化机制的分析.
- 蛋白质工程策略来调整活性构造并缩短化物转移距离.
- 使用工程Escherichia coli用于CHDA生产的全细胞生物催化剂.
主要成果:
- 确定了化物转移能量障碍 (13.4 和 20.4 kcal·mol-1),限制了野生型的AcCO效率.
- 开发了W4 (S101A/H351V/N378S/Q329N) 变种,用于CHDA生产,其催化效率提高了112.5倍.
- 在使用大肠杆菌全细胞催化剂的3L尺度制剂中,获得了29.6g·L-1标位和42.2%的CHDA产量.
结论:
- 蛋白质工程成功地降低了AOX中化物转移的能量屏障.
- 工程 AOX 变种 W4 显示了显著增强的 CHDA 生产能力.
- 开发的生物催化系统对工业规模的CHDA合成具有前景.
相关概念视频
Oxidations of Aldehydes and Ketones to Carboxylic Acids
3.9K
Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
3.9K
Oxidation of Alcohols
13.0K
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:
13.0K
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
3.6K
Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
3.6K
Aldehydes and Ketones with Alcohols: Hemiacetal Formation
6.1K
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.
6.1K
Preparation 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
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
10.1K
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.
10.1K


