Mao, S., Wang, X., Ge, Z., Su, A., Zhang, L., Li, Y., Liu, X., Lu, F. (2017). Microbial hydroxylation of 16α, 17α-epoxyprogesterone by Penicillium decumbens. Iranian Journal of Pharmaceutical Research, 16(3), 1161-1166. doi: 10.22037/ijpr.2017.2073
Shuhong Mao; Xuerong Wang; Zhijiang Ge; An Su; Lixia Zhang; Yanqing Li; Xiaoguang Liu; Fuping Lu. "Microbial hydroxylation of 16α, 17α-epoxyprogesterone by Penicillium decumbens". Iranian Journal of Pharmaceutical Research, 16, 3, 2017, 1161-1166. doi: 10.22037/ijpr.2017.2073
Mao, S., Wang, X., Ge, Z., Su, A., Zhang, L., Li, Y., Liu, X., Lu, F. (2017). 'Microbial hydroxylation of 16α, 17α-epoxyprogesterone by Penicillium decumbens', Iranian Journal of Pharmaceutical Research, 16(3), pp. 1161-1166. doi: 10.22037/ijpr.2017.2073
Mao, S., Wang, X., Ge, Z., Su, A., Zhang, L., Li, Y., Liu, X., Lu, F. Microbial hydroxylation of 16α, 17α-epoxyprogesterone by Penicillium decumbens. Iranian Journal of Pharmaceutical Research, 2017; 16(3): 1161-1166. doi: 10.22037/ijpr.2017.2073
Microbial hydroxylation of 16α, 17α-epoxyprogesterone by Penicillium decumbens
1College of Biotechnology, Tianjin University of Science and Technology
2Tianjin Key Laboratory of Industrial Microbiology, College of Biotechnology, Tianjin University of Science & Technology
3Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY, 12180, USA
4Key Laboratory of Industrial Fermentation Microbiology，Ministry of Education，Tianjin University of Science & Technology
5Key Laboratory of Industrial Fermentation Microbiology，Ministry of Education，Tianjin University of Science & Technology Tianjin Key Laboratory of Industrial Microbiology, College of Biotechnology, Tianjin University of Science & Technology,
Abstract
Microbial transformation has been successfully applied in the production of steroid intermediates with therapeutic use and commercial value in pharmaceutical industry due to its high regio- and stereo-selectivity. As such, it is still important to screen microbial strains with novel activity or more efficient abilities in the development of the commercial steroid industry. Biotransformation of steroid: 16α, 17α-epoxyprogesterone (EP) using Penicillium decumbens as biocatalyst was investigated and selective hydroxylation of EP was observed. The products were separated by flash chromatography, and the structure determination were performed by MS, NMR, and X-ray crystallography. Biotransformation of EP afforded 7β-hydroxy-16α, 17α-epoxyprogesterone 1 and 7β, 11α-dihydroxy-16α, 17α-epoxyprogesterone 2. The two novel metabolic products 1 and 2 were reported for the first time. Moreover, the identified C7β- and C11-α hydroxylation is a novel reaction of microbial transformation of steroids by P. decumbens. This indicated that P. decumbens was a potential strains to produce the valuable pharmaceutical ingredients and precursors.
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