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Chemical and Enzymatic Approaches to Carbohydrate-Derived Spiroketals: Di-D-Fructose Dianhydrides (DFAs)
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Profesor García González 1, 41012 Sevilla, Spain
Instituto de Investigaciones Químicas, CSIC – Universidad de Sevilla, Américo Vespucio 49, Isla de la Cartuja, 41092 Sevilla, Spain
* Author to whom correspondence should be addressed.
Received: 20 June 2008; in revised form: 22 July 2008 / Accepted: 28 July 2008 / Published: 12 August 2008
Abstract: Di-D-fructose dianhydrides (DFAs) comprise a unique family of stereoisomeric spiro-tricyclic disaccharides formed upon thermal and/or acidic activation of sucroseand/ or D-fructose-rich materials. The recent discovery of the presence of DFAs in food products and their remarkable nutritional features has attracted considerable interest from the food industry. DFAs behave as low-caloric sweeteners and have proven to exert beneficial prebiotic nutritional functions, favouring the growth of Bifidobacterium spp. In the era of functional foods, investigation of the beneficial properties of DFAs has become an important issue. However, the complexity of the DFA mixtures formed during caramelization or roasting of carbohydrates by traditional procedures (up to 14 diastereomeric spiroketal cores) makes evaluation of their individual properties a difficult challenge. Great effort has gone into the development of efficient procedures to obtain DFAs in pure form at laboratory and industrial scale. This paper is devoted to review the recent advances in the stereoselective synthesis of DFAs by means of chemical and enzymatic approaches, their scope, limitations, and complementarities.
Keywords: spirocompounds; stereoselective synthesis; difructose dianhydrides; fructose; inulin; levan.
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García-Moreno, M.I.; Benito, J.M.; Mellet, C.O.; Fernández, J.M.G. Chemical and Enzymatic Approaches to Carbohydrate-Derived Spiroketals: Di-D-Fructose Dianhydrides (DFAs). Molecules 2008, 13, 1640-1670.
García-Moreno MI, Benito JM, Mellet CO, Fernández JMG. Chemical and Enzymatic Approaches to Carbohydrate-Derived Spiroketals: Di-D-Fructose Dianhydrides (DFAs). Molecules. 2008; 13(8):1640-1670.
García-Moreno, M. I.; Benito, Juan M.; Mellet, Carmen O.; Fernández, José M.G. 2008. "Chemical and Enzymatic Approaches to Carbohydrate-Derived Spiroketals: Di-D-Fructose Dianhydrides (DFAs)." Molecules 13, no. 8: 1640-1670.