Improved chemoenzymatic asymmetric synthesis of (S)-Rivastigmine
| Autor: | Johann H. Sattler, Mathias Pickl, Wilfried Banko, Wolfgang Kroutil, Dominik Koszelewski, Katharina Tauber, Kurt Faber, Michael Fuchs, Anja K. Holzer |
|---|---|
| Rok vydání: | 2012 |
| Předmět: |
chemistry.chemical_classification
Carbamate biology Transamination Stereochemistry medicine.medical_treatment Organic Chemistry Enantioselective synthesis biology.organism_classification Biochemistry chemistry Biocatalysis Drug Discovery medicine Side chain Amine gas treating Paracoccus denitrificans Pharmacophore |
| Zdroj: | Tetrahedron. 68:7691-7694 |
| ISSN: | 0040-4020 |
| Popis: | (S)-Rivastigmine [(S)-1] was obtained via a four-step synthesis using an asymmetric enzymatic transamination protocol as the key step. An early introduction of the carbamate pharmacophore side chain avoided the use of protective group strategies and hence led to a considerable shortcut. This strategy required a novel ω-transaminase from Paracoccus denitrificans, which could transform the highly polar key substrate 3-acetylphenyl ethyl(methyl)carbamate (4) to the corresponding amine (S)-5 in 99% ee and >80% conversion. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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