Regio- and enantioselective O-demethylation of tetrahydroprotoberberines by cytochrome P450 enzyme system from Streptomyces griseus ATCC 13273

Shen, Chen; Shan, Tianyue; Zhao, Wanli; Ou, Chenhui; Li, Li; Liu, Xiufeng; Liu, Jihua; Yu, Boyang

doi:10.1007/s00253-018-9416-4

Cited by 5 publications

(4 citation statements)

References 47 publications

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“…There are Eighteen cytochromes P450 (CYP) in Streptomyces coelicolor A3(2) (Lamb et al, 2002), 33 cytochromes P450 (CYPs) in the avermectin‐producing bacterium Streptomyces avermitilis (Lamb et al, 2003), 27 P450S in Streptomyces griseus IFO 13350 (Makino et al, 2014) and 15 P450s in Streptomyces peucetius ATCC 27952 which produces clinically important anthracycline chemotherapeutic agents (Parajuli et al, 2004). In our previously study, we also identified 27 P450s in Streptomyces griseus ATCC 13273 (Shen et al, 2019b). With the rapid expansion of genome sequencing, the number of Streptomyces P450 is also rapidly growing.…”

Section: Microbial P450omesmentioning

confidence: 75%

“…In our study, varies substrates were studied for CYP105D1 biotransformation. CYP105D1 exhibited markedly regioselective demethylation of nonhydroxyl‐THPBs and monohydroxyl‐THPBs on the D‐ring (Shen et al, 2019b). And also used for the regioselective demethylation of papaverine at C‐6 (Shen et al, 2019c).…”

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

confidence: 99%

“…In the whole‐cell catalytic system, by co‐expressing the electron transport protein corresponding to the cytochrome P450 enzyme, the catalytic efficiency of the whole‐cell system can be effectively improved (Liu et al, 2022). In our previous studies, the homologous redox partner of CYP105D1 from streptomyces griseus ATCC 13273 was selected, a homologous redox partner Fdr1560/soyB was identified to enhance the catalytic efficiency of the CYP105D1‐based whole‐cell system (Shen et al, 2019b). Chrispian et al screened different yeast species for coexpression of P450 and P450‐reductase (CPR) partners, using CYP53B1 from Rhodotorula minuta as an exemplary P450 (Theron et al, 2019).…”

Section: Promising Strategy For Using Microbial P450s In Industrymentioning

confidence: 99%

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

Wang,

Pan,

Wang

et al. 2023

Biotech & Bioengineering

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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.

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Section: Microbial P450omesmentioning

confidence: 75%

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

confidence: 99%

Section: Promising Strategy For Using Microbial P450s In Industrymentioning

confidence: 99%

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

Wang,

Pan,

Wang

et al. 2023

Biotech & Bioengineering

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“…CYP105D1 has been simulated in our previous study . The default parameters of MOE‐Dock program were used for the molecular docking of the ligands.…”

Section: Methodsmentioning

confidence: 99%

Specific N‐demethylation of verapamil by cytochrome P450 from Streptomyces griseus ATCC 13273

Shen

Liu

Dai

et al. 2019

Engineering in Life Sciences

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Norverapamil, the N‐demethylated derivative of verapamil, is a novel promising leading compound for attenuating multidrug resistance with less side effects compared with verapamil. However, the efficient synthetic method for norverapamil is absent. In this study, an innovative biotechnological method based on enzymatic catalysis was presented for the high‐efficient production of norverapamil. CYP105D1, a cytochrome P450 from Streptomyces griseus ATCC 13273, was identified to carry out a one‐step specific N‐demethylation of verapamil along with putidaredoxin reductase (Pdr) and putidaredoxin (Pdx) as the redox partner. Docking calculations rationalized the specific N‐demethylation observed in experiment and identified important amino acid residues for verapamil binding. Furthermore, a CYP105D1‐based whole‐cell system in E. coli BL21(DE3) was established and optimized for highly efficient N‐demethylation of verapamil. The bioconversion rate of verapamil by the whole cell system came up to 60.16% within 24 hours under the optimized conditions. These results demonstrated the high potential of CYP105D1‐based biocatalytic system for norverapamil production.

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Recent Progress on Peroxidase Modification and Application

Shen,

Wang

2024

Appl Biochem Biotechnol

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Regio- and enantioselective O-demethylation of tetrahydroprotoberberines by cytochrome P450 enzyme system from Streptomyces griseus ATCC 13273

Cited by 5 publications

References 47 publications

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

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

Specific N‐demethylation of verapamil by cytochrome P450 from Streptomyces griseus ATCC 13273

Recent Progress on Peroxidase Modification and Application

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