作为抗激素和抗微生物剂的天然酸的两步流动化
Desirée Pecora1, Anna M Magni1, Sara Vicinanza1
1Department of Pharmaceutical Sciences, University of Milan, Via Mangiagalli 25, 20133 Milan, Italy.
Journal of natural products
|March 31, 2025
概括
一种新的两步化学酶流方法有效合成酸胺酸 (HCAAs) 和利帕林衍生物. 这种可持续的方法产生了具有显著激素清除,抗菌和抗莱什曼特性的化合物.
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.
- 流动化学 流动化学
背景情况:
- 天然基胺酸胺基 (HCAAs) 和利帕林具有宝贵的健康益处.
- 从自然资源中提取是具有挑战性的,传统的合成方法是低效和浪费的.
- 需要可持续和高效的合成途径来获得这些化合物.
研究的目的:
- 开发一种新的两步化学酶流方法,用于合成HCAAs和利帕林衍生物.
- 使用固定催化剂优化化和化过程.
- 评估合成化合物的生物活性.
主要方法:
- 使用固定的SiliaBond托西克酸 (SCX-3) 进行流式费舍尔化.
- 流动化由固定 *Candida antarctica* 脂酶 B. 催化.
- 反应条件的优化,包括停留时间和溶剂 (烯).
主要成果:
- 在短暂的停留时间内实现化香酸的定量产量.
- 通过化学酶流过程成功合成胺.
- 合成的化合物表现出激素清除,抗菌和抗莱什曼活动.
结论:
- 开发的两步化学酶流法为HCAA和利帕林衍生物合成提供了高效和可持续的替代方案.
- 合成的化合物表现出有前途的生物特性,需要进一步研究.
- 这种方法在合成有价值的生物活性分子方面推进了绿色化学原理.
相关概念视频
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
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.
Oxidation of Phenols to Quinones
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Radical Formation: Addition
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an unpaired...
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an unpaired...
Radical Formation: Elimination
Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect to...
Radical Autoxidation
The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
Radical Chain-Growth Polymerization: Overview
Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...


