Efficient synthesis of the ketone body ester (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrate and its (S,S) enantiomer
| Autor: | Noah Budin, Cassidy Raab, Scott M. Ulrich, Erin Leigh Higgins, Anthony DiBernardo, Chun Li |
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| Rok vydání: | 2018 |
| Předmět: |
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Molecular 0301 basic medicine Stereochemistry Hydroxybutyrates Biochemistry Fungal Proteins 03 medical and health sciences Hydrolysis 4-Butyrolactone Drug Discovery Lipase Molecular Biology Candida 3-Hydroxybutyric Acid Esterification biology Chemistry Organic Chemistry Enantioselective synthesis Stereoisomerism Ketones Enzymes Immobilized biology.organism_classification 030104 developmental biology Butanediol biology.protein Ketone bodies Candida antarctica Enantiomer |
| Zdroj: | Bioorganic Chemistry. 80:560-564 |
| ISSN: | 0045-2068 |
| DOI: | 10.1016/j.bioorg.2018.07.010 |
| Popis: | The ketone body ester (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrate and its (S,S) enantiomer were prepared in a short, operationally simple synthetic sequence from racemic β-butyrolactone. Enantioselective hydrolysis of β-butyrolactone with immobilized Candida antarctica lipase-B (CAL-B) results in (R)-β-butyrolactone and (S)-β-hydroxybutyric acid, which are easily converted to (R) or (S)-ethyl-3-hydroxybutyrate and reduced to (R) or (S)-1,3 butanediol. Either enantiomer of ethyl-3-hydroxybutyrate and 1,3 butanediol are then coupled, again using CAL-B, to produce the ketone body ester product. This is an efficient, scalable, atom-economic, chromatography-free, and low cost synthetic method to produce the ketone body esters. |
| Databáze: | OpenAIRE |
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