Chemical and enzymatic approaches to carbohydrate-derived spiroketals: di-D-fructose dianhydrides (DFAs).
Di-D-fructose dianhydrides (DFAs) comprise a unique family of stereoisomeric spiro-tricyclic disaccharides formed upon thermal and/or acidic activation of sucrose- and/ 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.
García-Moreno
M Isabel
MI
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Profesor García González 1, 41012 Sevilla, Spain. isagar@us.es
Benito
Juan M
JM
Mellet
Carmen Ortiz
CO
Fernández
José M García
JM
D000812:Anhydrides / Q000138:chemical synthesis*; D002241:Carbohydrates / Q000737:chemistry; D019649:Food Industry; D005632:Fructose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005663:Furans / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*
D000812:Anhydrides; D002241:Carbohydrates; D005663:Furans; D013141:Spiro Compounds; C520774:spiroketal; D005632:Fructose
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