Fructose 1,6-diphosphate aldolase-catalysed stereoselective C–C bond formation
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 2669-2673
- https://doi.org/10.1039/p19910002669
Abstract
Fructose 1,6-diphosphate aldolase has been used as a catalyst for the synthesis (1–15 mmol scales) of several unusual sugar derivatives, including 5-deoxy-D-fructose, 6-deoxy-6-chloro-D-fructose, 6-deoxy-6-vinyl-D-fructose, 5,7-dideoxy-7-azido-L-xylo-heptulose, 5-deoxy-L-xylo-heptulose, 5,7-dideoxy-7-amino-L-xylo-heptulose and 5-deoxy-5-acetamido-L-xylo-hexulose.Keywords
This publication has 17 references indexed in Scilit:
- Enzyme-catalyzed aldol condensation for asymmetric synthesis of azasugars: synthesis, evaluation, and modeling of glycosidase inhibitorsJournal of the American Chemical Society, 1991
- Enzyme-catalyzed reactions. Part 4. Aldolase-catalyzed carbon-carbon bond formation for stereoselective synthesis of nitrogen containing carbohydratesThe Journal of Organic Chemistry, 1990
- Use of a recombinant bacterial fructose-1,6-diphosphate aldolase in aldol reactions: preparative syntheses of 1-deoxynojirimycin, 1-deoxymannojirimycin, 1,4-dideoxy-1,4-imino-D-arabinitol, and fagomineJournal of the American Chemical Society, 1989
- Cloning, sequence analysis and over-expression of the gene for the class II fructose 1,6-bisphosphate aldolase of Escherichia coliBiochemical Journal, 1989
- Enzyme-catalyzed synthesis of carbohydratesTetrahedron, 1989
- Rabbit muscle aldolase as a catalyst in organic synthesisJournal of the American Chemical Society, 1989
- A combined chemical and enzymatic procedure for the synthesis of 1-deoxynojirimycin and 1-deoxymannojirimycinTetrahedron Letters, 1988
- Fructose 1,6-diphosphate aldolase-catalyzed stereoselective synthesis of C-alkyl and N-containing sugars: thermodynamically controlled C-C bond formationsThe Journal of Organic Chemistry, 1988
- Enzyme‐Catalyzed Synthesis of 1‐Deoxymannojirimycin, 1‐Deoxynojirimycin, and 1,4‐Dideoxy‐1,4‐imino‐D‐arabinitolAngewandte Chemie International Edition in English, 1988
- Structure–sweetness relationships for fructose analogs. Part I. Synthesis and evaluation of sweetness of 5-deoxy-D-threo-hexuloseCanadian Journal of Chemistry, 1982