One-pot enantioselective synthesis of (S)-spirobrassinin and non-natural (S)-methylspirobrassinin from amino acids using a turnip enzyme
| Autor: | Kaori Ryu, Seikou Nakamura, Souichi Nakashima, Hisashi Matsuda |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
inorganic chemicals
Stereochemistry 01 natural sciences Catalysis Spiro Compounds Amino Acids chemistry.chemical_classification biology 010405 organic chemistry Plant Extracts Phytoalexin Brassica napus Enantioselective synthesis food and beverages Brassicaceae Stereoisomerism biology.organism_classification 0104 chemical sciences Amino acid 010404 medicinal & biomolecular chemistry Thiazoles Enzyme chemistry Reagent Molecular Medicine Spirobrassinin |
| Zdroj: | Journal of natural medicines. 75(2) |
| ISSN: | 1861-0293 |
| Popis: | The enantioselective synthesis of (S)-(-)-spirobrassinin, which features a unique sulfur-containing spirooxindole skeleton, was achieved by focusing on the phytoalexin generation in Brassicaceae plants. Specifically, (S)-(-)-spirobrassinin was obtained in a one-pot fashion from L-tryptophan through a reaction involving S-spirocyclization with various turnip enzymes and constituents, i.e., using the turnip as a reaction reagent, catalyst, and reaction vessel. Surprisingly, this strategy also enabled the one-pot enantioselective synthesis of the novel non-natural spirooxindole (S)-(-)-5-methylspirobrassinin from 5-methyl-DL-tryptophan. |
| Databáze: | OpenAIRE |
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