Hydroxylation, Epoxidation, and Dehydrogenation of Capsaicin by a Microbial Promiscuous Cytochrome P450 105D7

Ma, Bingbing; Wang, Qianwen; Han, Bingnan; Ikeda, Haruo; Zhang, Chunfang; Xu, Lian‐Hua

doi:10.1002/cbdv.202000910

Cited by 4 publications

(4 citation statements)

References 42 publications

(61 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In conclusion, in the powerful family of P450 enzymes, there are a variety of alkene epoxidase enzymes, which have great potential in catalyzing multiple types of alkenes, and can catalyze the alkene epoxidation of a variety of natural products and biologically active molecules, including the epoxidation of unsaturated aliphatic olefins, [74,75] macrolide olefin substrates such as mycinamicin, [76][77][78][79] nitro polycyclic aromatic hydrocarbons, [80] and capsaicin natural product, [63,81] etc.…”

Section: Other P450 Monooxygenasesmentioning

confidence: 99%

Asymmetric Bio‐epoxidation of Unactivated Alkenes

Wang

et al. 2023

ChemBioChem

View full text Add to dashboard Cite

Optically active epoxides play important roles in pharmaceutical, agricultural and fine chemical syntheses. There are many chiral medications with pharmacodynamic activity in nature that can be synthesized by chiral epoxides. In recent years, researchers have developed a variety of biocatalysts for the asymmetric epoxidation of alkenes, which use oxygen or hydrogen peroxide as eco-friendly and low-cost oxidants, to provide better chemo-, regio-and stereoselectivity under moderate reaction conditions. In this paper, the advances, opportunities and challenges of the asymmetric epoxidation of unactive alkenes by biocatalyst are reviewed.

show abstract

Section: Other P450 Monooxygenasesmentioning

confidence: 99%

Asymmetric Bio‐epoxidation of Unactivated Alkenes

Wang

et al. 2023

ChemBioChem

View full text Add to dashboard Cite

show abstract

“…CYP105D7 was identified from streptomyces avermitilis MA4680. It was found that CYP105D7 catalyzes hydroxylation, epoxidation and dehydrogenation of capsaicin (Ma et al, 2021). And also catalyzes hydroxylation of diclofenac at the C4’‐position (Xu et al, 2015).…”

Section: Application Potential Of Microbial P450s In Drug Production ...mentioning

confidence: 99%

Microbial P450 repertoire (P450ome) and its application feasibility in pharmaceutical industry, chemical industry, and environmental protection

Wang,

Pan,

Wang

et al. 2023

Biotech & Bioengineering

View full text Add to dashboard Cite

Cytochrome P450s (CYPs) are heme‐thiolated enzymes that catalyze the oxidation of C‐H bonds in a regio‐ and stereo‐selective manner. CYPs are widely present in the biological world. With the completion of more biological genome sequencing, the number and types of P450 enzymes have increased rapidly. P450 in microorganisms is easy to clone and express, rich in catalytic types, and strong in substrate adaptability, which has good application potential. Although the number of P450 enzymes found in microorganisms is huge, the function of most of the microorganism P450s has not been studied, and it contains a large number of excellent biocatalysts to be developed. This review is based on the P450 groups in microorganisms. First, it reviews the distribution of P450 groups in different microbial species, and then studies the application of microbial P450 enzymes in the pharmaceutical industry, chemical industry and environmental pollutant treatment in recent years. And focused on the application fields of P450 enzymes of different families to guide the selection of suitable P450s from the huge P450 library. In view of the current shortcomings of microbial P450 in the application process, the final solution is the most likely to assist the application of P450 enzymes in large‐scale, that is, whole cell transformation combined with engineering, fusion P450 combined with immobilization technology.

show abstract

“…Based on the metabolism studies of capsaicin (40) by Tian et al (2019) found the P450 enzyme CYP105D7 from Streptomyces avermitilis could be a catalyst for the oxidation of the capsaicin (40), which is a pain reliever and also has activities of anti-tumor, anti-obesity, and cardio-protection. In this reaction ( Figure 2N ), three products were generated, with the majority being obtained by ω -1 allylic hydroxylation at a yield of 64% (40b), the alkyl dehydrogenation product at a yield of 23% (40c), and the epoxidation product at a yield of 13% (40a) ( Ma et al, 2021 ).…”

Section: P450smentioning

confidence: 99%

Enzyme-catalyzed allylic oxidation reactions: A mini-review

et al. 2022

View full text Add to dashboard Cite

Chiral allylic oxidized products play an increasingly important role in the pharmaceutical, agrochemical, and pharmaceutical industries. Biocatalytic C–H oxyfunctionalization to synthesize allylic oxidized products has attracted great attention in recent years, with the ability to simplify synthetic approaches toward complex compounds. As a result, scientists have found some new enzymes and mutants through techniques of gene mining and enzyme-directed evolution in recent years. This review summarizes the recent developments in biocatalytic selective oxidation of olefins by different kinds of biocatalysts.

show abstract

Hydroxylation, Epoxidation, and Dehydrogenation of Capsaicin by a Microbial Promiscuous Cytochrome P450 105D7

Cited by 4 publications

References 42 publications

Asymmetric Bio‐epoxidation of Unactivated Alkenes

Asymmetric Bio‐epoxidation of Unactivated Alkenes

Microbial P450 repertoire (P450ome) and its application feasibility in pharmaceutical industry, chemical industry, and environmental protection

Enzyme-catalyzed allylic oxidation reactions: A mini-review

Contact Info

Product

Resources

About