Combined chemoenzymatic synthesis of 20-6-deoxy-α-L-sorbofuranosyl-D-glucose
| Autor: | Marita Grothus, Lothar Elling, Hans-Peter Brockamp, Maria-Regina Kula, Alois Steigel, Torsten Minuth, Jörg Peters |
|---|---|
| Rok vydání: | 1993 |
| Předmět: |
chemistry.chemical_classification
biology Carbonyl Reductase Stereochemistry Organic Chemistry Aldolase A Disaccharide Fructose biology.organism_classification Aldehyde Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry D-Glucose biology.protein Physical and Theoretical Chemistry Dihydroxyacetone phosphate Staphylococcus carnosus |
| Zdroj: | Tetrahedron: Asymmetry. 4:1173-1182 |
| ISSN: | 0957-4166 |
| Popis: | The chemoenzymatic synthesis of 20-6-deoxy-α-L-sorbofuranosyl-D-glucuse has been performed by coupling four enzymatic and one simple chemical step on a preparative scale with 17% overall yield. At first, pyruvic aldehyde dimethyl acetal was reduced stereospecifically to L-lactaldehyde dimethyl acetal by the carbonyl reductase from Candida parapsilosis with approximately 100% ee. Subsequently, the product was converted to L-lactaldehyde by simple treatment with a strong cation exchanger. Secondly, stereoselective condensation between dihydroxyacetone phosphate and L-lactaldehyde was catalyzed by fructose 1,6-bisphosphate aldolase from Staphylococcus carnosus. The resulting sugar phosphate was dephosphorylated by acid phosphatase treatment and further purified by cation exchange chromatography. The structure and stereochemistry of the product, 6-deoxy-L-sorbose, was confirmed by 1H- and 13C-NMR analysis. In the last step sucrose synthase from rice grains was utilized to catalyze the transfer of glucose from UDP-glucose to 6-deoxy-L-sorbose. The structure and stereochemistry of the disaccharide formed, 20-6-deoxy-a-L-sorbofuranosyl-D-glucose, was also confirmed by 1H- and 13C-NMR analysis. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|