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相关概念视频

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.8K
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.
10.8K
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

11.2K
In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
11.2K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

6.1K
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.
6.1K
Preparation of Epoxides03:00

Preparation of Epoxides

8.1K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
8.1K
Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

8.0K
Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
8.0K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.0K
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.
9.0K

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计算机设计的过氧酶表现出多样化和选择性的烯氧功能化.

Judith Münch1, Jordi Soler2, Ofir Gildor-Cristal3

  • 1Institute of Chemistry, Martin Luther-University Halle-Wittenberg, Weinbergweg 22, Halle (Saale) 06120, Germany.

ACS catalysis
|August 7, 2025
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概括

计算式酶设计迅速创造了50种不特定的过氧酶 (MthUPO) 变体,具有增强的烯氧功能. 这些设计的酶显著提高了活性,选择性和新产品合成,在各种应用中表现优于野生类型.

关键词:
这就是FuncLib的功能.这种植物是Saccharomyces cerevisiae.计算化学计算化学酶是一种酶.氧功能化的氧功能化.它们是烯 (terpenes).不特定的过氧酶酶.酵母酵母是一种酵母.

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科学领域:

  • 生物催化和酶工程 生物催化和酶工程
  • 计算化学和分子建模计算化学和分子建模
  • 有机合成和化学转化

背景情况:

  • 烯的选择性氧功能化对于工业合成至关重要,但仍然具有挑战性.
  • 非特异性过氧酶 (UPO) 具有潜力,但往往缺乏所需的选择性和活性.
  • 计算酶设计为设计具有定制功能的生物催化剂提供了一条途径.

研究的目的:

  • 为了计算设计MthUPO的变体,改进了氧功能化能力.
  • 为了增强酶活性,区域选择性,化学选择性和特定基质的立体选择性.
  • 为了证明在生物催化剂开发中导酶工程的有效性.

主要方法:

  • 利用MthUPO的AlphaFold2模型作为计算设计的基础.
  • 采用FuncLib算法生成一个包含50个酶变体的库.
  • 进行了广泛的基质测试,以评估设计变体的活性和选择性概况.

主要成果:

  • 所有50种设计的变体都保持了可测量的活性,在基质上观察到显著的改善 (增加了2.2倍至7.1倍).
  • 选择性显著变化,包括对3-基β-达马斯康的区域选择性增加 (3%至46%) 和对甲醇A (>99%) 和乙醇B (89%) 的化学选择性增加.
  • 实现了新型产品合成 (例如,异皮醇,环氧化物) 和对β-离子离子基化进行反转的反离子选择性 (R:S比1:99).

结论:

  • 启用FuncLib的活跃站点改造成功生成了一个小而多样化的酶面板,其性能优于野生型MthUPO.
  • 计算设计,特别是在设计4和11等变体中利用表观效应,使得高度选择性的生物催化剂的快速开发成为可能.
  • 在 silico 方法是强大的工具,可以为具有挑战性的合成应用程序创建定制的酶.