Enantiodivergent Synthesis of Halofuginone by Candida antarctica Lipase B (CAL-B)-Catalyzed Kinetic Resolution in Cyclopentyl Methyl Ether (CPME)
| Autor: | Ernesto G. Occhiato, Elia Maffeis, Elisa De Marchi, Dina Scarpi, Davide Arnodo, Cristina Prandi |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
biocatalysis
Materials Science (miscellaneous) Cyclopentyl methyl ether 010402 general chemistry 01 natural sciences Catalysis Kinetic resolution Biomaterials chemistry.chemical_compound halofuginone lipase Organic chemistry kinetic resolution Lipase QD1-999 biology 010405 organic chemistry Organic Chemistry biology.organism_classification 0104 chemical sciences Solvent Chemistry chemistry Biocatalysis Reagent biology.protein Candida antarctica Enantiomer |
| Zdroj: | SynOpen, Vol 05, Iss 02, Pp 145-151 (2021) |
| ISSN: | 2509-9396 |
| DOI: | 10.1055/a-1523-6428 |
| Popis: | The synthesis of both enantiomers of a key intermediate in the synthesis of halofuginone was accomplished by a Candida antarctica lipase B (CAL-B)-catalyzed kinetic resolution of the corresponding racemate. When the resolution was carried out in the versatile solvent cyclopentyl methyl ether (CPME) using p-chlorophenylbutyrate (PCPB) as the acylating reagent, the highest enantiomeric ratio (E) values were measured, and highly enantioenriched (95% ee) compounds could be obtained in a single iteration. As an example, one of the two enantiomers was used as a starting material to prepare (+)-halofuginone in a three-step procedure. |
| Databáze: | OpenAIRE |
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