Regioselective C-H hydroxylation of omeprazole sulfide by Bacillus megaterium CYP102A1 to produce a human metabolite |
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Authors: | Hyun-Hee Jang Sang-Hoon Ryu Thien-Kim Le Tiep Thi My Doan Thi Huong Ha Nguyen Ki Deok Park Da-Eun Yim Dong-Hyun Kim Choong-Kyung Kang Taeho Ahn Hyung-Sik Kang Chul-Ho Yun |
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Affiliation: | 1.School of Biological Sciences and Technology,Chonnam National University,Gwangju,Republic of Korea;2.Gwangju Center,Korea Basic Science Institute,Gwangju,Republic of Korea;3.Department of Pharmacology and Pharmacogenomics Center,Inje University College of Medicine,Busan,Republic of Korea;4.Hoseo University,Asan-si,Republic of Korea;5.College of Veterinary Medicine,Chonnam National University,Gwangju,Republic of Korea |
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Abstract: | ObjectivesTo find a simple enzymatic strategy for the efficient synthesis of the expensive 5′-hydroxyomeprazole sulfide, a recently identified minor human metabolite, from omeprazole sulfide, which is an inexpensive substrate.ResultsThe practical synthetic strategy for the 5′-OH omeprazole sulfide was accomplished with a set of highly active CYP102A1 mutants, which were obtained by blue colony screening from CYP102A1 libraries with a high conversion yield. The mutant and even the wild-type enzyme of CYP102A1 catalyzed the high regioselective (98 %) C-H hydroxylation of omeprazole sulfide to 5′-OH omeprazole sulfide with a high conversion yield (85–90 %).ConclusionsA highly efficient synthesis of 5′-OH omeprazole sulfide was developed using CYP102A1 from Bacillus megaterium as a biocatalyst. |
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