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A Novel 3-Phytosterone-9α-Hydroxylase Oxygenation Component and Its Application in Bioconversion of 4-Androstene-3,17-Dione to 9α-Hydroxy-4-Androstene-3,17-Dione Coupling with A NADH Regeneration Formate Dehydrogenase

1
The Key Laboratory of Industrial Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, 1800 Liu Avenue, Wuxi 214122, Jiangsu, China
2
Biochemical Engineering College, Beijing Union University, Beijing 100023, China
3
School of Food Science and Technology, Jiangnan University, 1800 Liu Avenue, Wuxi 214122, Jiangsu, China
4
School of Medicine, Yichun University, Yichun 336000, Jiangxi, China
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(14), 2534; https://doi.org/10.3390/molecules24142534
Received: 22 May 2019 / Revised: 1 July 2019 / Accepted: 9 July 2019 / Published: 11 July 2019
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Abstract

9α-Hydroxy-4-androstene-3,17-dione (9-OH-AD) is one of the significant intermediates for the preparation of β-methasone, dexamethasone, and other steroids. In general, the key enzyme that enables the biotransformation of 4-androstene-3,17-dione (AD) to 9-OH-AD is 3-phytosterone-9α-hydroxylase (KSH), which consists of two components: a terminal oxygenase (KshA) and ferredoxin reductase (KshB). The reaction is carried out with the concomitant oxidation of NADH to NAD+. In this study, the more efficient 3-phytosterone-9α-hydroxylase oxygenase (KshC) from the Mycobacterium sp. strain VKM Ac-1817D was confirmed and compared with reported KshA. To evaluate the function of KshC on the bioconversion of AD to 9-OH-AD, the characterization of KshC and the compounded system of KshB, KshC, and NADH was constructed. The optimum ratio of KSH oxygenase to reductase content was 1.5:1. An NADH regeneration system was designed by introducing a formate dehydrogenase, further confirming that a more economical process for biological transformation from AD to 9-OH-AD was established. A total of 7.78 g of 9-OH-AD per liter was achieved through a fed-batch process with a 92.11% conversion rate (mol/mol). This enzyme-mediated hydroxylation method provides an environmentally friendly and economical strategy for the production of 9-OH-AD. View Full-Text
Keywords: 9α-Hydroxy-4-androstene-3,17-dione; 3-phytosterone-9α-hydroxylase; hydroxylation; NADH regeneration 9α-Hydroxy-4-androstene-3,17-dione; 3-phytosterone-9α-hydroxylase; hydroxylation; NADH regeneration
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Zhang, X.; Zhu, M.; Han, R.; Zhao, Y.; Chen, K.; Qian, K.; Shao, M.; Yang, T.; Xu, M.; Xu, J.; Rao, Z. A Novel 3-Phytosterone-9α-Hydroxylase Oxygenation Component and Its Application in Bioconversion of 4-Androstene-3,17-Dione to 9α-Hydroxy-4-Androstene-3,17-Dione Coupling with A NADH Regeneration Formate Dehydrogenase. Molecules 2019, 24, 2534.

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