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Molecules 2008, 13(8), 1640-1670; doi:10.3390/molecules13071640
Review

Chemical and Enzymatic Approaches to Carbohydrate-Derived Spiroketals: Di-D-Fructose Dianhydrides (DFAs)

1,* , 2
,
1 and 2
Received: 20 June 2008 / Revised: 22 July 2008 / Accepted: 28 July 2008 / Published: 12 August 2008
(This article belongs to the Special Issue Spiro Compounds)
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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. spirocompounds; stereoselective synthesis; difructose dianhydrides; fructose; inulin; levan.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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