Novel biocatalyst for productions of S-(-)-2-[6-benzyloxy -2,5,7,8-tetramethylchroman -2-yl] ethanol—precursor of natural α-tocols
| Autor: | N. I. Petukhova, V. V. Zorin, I. I. Kon’shina, V. N. Odinokov, A. Yu. Spivak |
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| Rok vydání: | 2017 |
| Předmět: |
Ethanol
010405 organic chemistry Enantioselective synthesis Substrate (chemistry) 010402 general chemistry Phosphate 01 natural sciences Applied Microbiology and Biotechnology Biochemistry 0104 chemical sciences chemistry.chemical_compound Hydrolysis chemistry Biocatalysis Yield (chemistry) Acetone Organic chemistry |
| Zdroj: | Applied Biochemistry and Microbiology. 53:187-193 |
| ISSN: | 1608-3024 0003-6838 |
| Popis: | A novel promising strain of actinobacteria Rhodococcus sp. 77-32 was identified. Its acetonetreated biomass the could be used as a biocatalyst for production of S-(-)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl] ethanol (S-BCE), a precursor of natural α-tocols. It was established that a reaction of enantioselective hydrolysis of racemic (±)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman (BCEA) occurred in the phosphate buffer–acetone system, resulting in enrichment of the residual substrate by S-enantiomer (S-(+)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman, S-BCEA). It was shown that the hydrolysis was accompanied by stereoinversion of the formed product, R-(+)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl] ethanol (R-BCE), into the S-BCE. The transformation conditions (acetone content, acidity, temperature, reaction duration) were optimized, providing simultaneous production of optically pure S-BCE and S-BCEA with an almost quantitative yield. |
| Databáze: | OpenAIRE |
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