Optically-active dihydropyridines via lipase-catalyzed enantioselective hydrolysis
| Autor: | Charles J. Sih, Loreto Salazar |
|---|---|
| Rok vydání: | 1995 |
| Předmět: |
biology
Chemistry Stereochemistry Organic Chemistry Pseudomonas Dihydropyridine Enantioselective synthesis Optically active biology.organism_classification Candida cylindracea Catalysis Inorganic Chemistry Hydrolysis biology.protein medicine Organic chemistry Physical and Theoretical Chemistry Lipase medicine.drug |
| Zdroj: | Tetrahedron: Asymmetry. 6:2917-2920 |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/0957-4166(95)00386-x |
| Popis: | Several prochiral esters of 1,4-dihydropyridines were enantioselectively hydrolyzed by Pseudomonas lipases (AK, P-30, and K-10) and Candida cylindracea lipase (OF-360). The stereochemical preferences of the lipases P-30 and K-10 were found to be always 4-Pro R and that of OF-360 to be 4-Pro S. In contrast, the prochiral preference of the lipase AK varied depending on the substitution on the dihydropyridine ring. The N-methoxymethyl derivatives afforded the 4S isomers (95% ee) whereas the N-unsubstituted compounds yielded the 4R isomers (50–70% ee). |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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