Regioselective C-H hydroxylation of omeprazole sulfide by Bacillus megaterium CYP102A1 to produce a human metabolite
| Autor: | Ki Deok Park, Daeun Yim, Hyun-Hee Jang, Thi Huong Ha Nguyen, Tiep Thi My Doan, Hyung-Sik Kang, Dong-Hyun Kim, Choong-Kyung Kang, Thien-Kim Le, Taeho Ahn, Chul-Ho Yun, Sang-Hoon Ryu |
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| Rok vydání: | 2016 |
| Předmět: |
0301 basic medicine
Sulfide Metabolite Bioengineering Hydroxylation 01 natural sciences Applied Microbiology and Biotechnology Catalysis 03 medical and health sciences chemistry.chemical_compound Bacterial Proteins Cytochrome P-450 Enzyme System Organic chemistry Humans Bacillus megaterium NADPH-Ferrihemoprotein Reductase chemistry.chemical_classification biology Chemistry 010401 analytical chemistry Substrate (chemistry) Stereoisomerism General Medicine biology.organism_classification 0104 chemical sciences 030104 developmental biology Enzyme Biocatalysis Yield (chemistry) Omeprazole Biotechnology |
| Zdroj: | Biotechnology letters. 39(1) |
| ISSN: | 1573-6776 |
| Popis: | To 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. The 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 %). A highly efficient synthesis of 5′-OH omeprazole sulfide was developed using CYP102A1 from Bacillus megaterium as a biocatalyst. |
| Databáze: | OpenAIRE |
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