Abstract
1,5-Anhydro-D-fructose (AF) is a valuable chiral building block for organic synthesis.[1] However, the antioxidant and antimicrobial properties of AF are equally important.[1] Due to these interesting properties AF is heavily patented for the use in pharmaceuticals, foods and cosmetics.
However, the preparation of AF, as well as 1,5- and 1,4-anhydroketoses in general, is still a challenging task.
An a-1,4-glycan lyase which degrades starch into AF has been identified, cloned and expressed in bacteria [2] but this fact does not yet give access to AF on a commercial basis. Neither are efficient chemical methods available despite the fact that the first low-yielding procedure by Lichtenthaler et al. was already described in 1980.[3]
In this presentation we will show new and efficient chemical methods employing easily available and cheap starting materials for the synthesis of 1,5- and 1,4-anhydroketoses as well as for derivatives and analogues thereof.
The potential of AF will be highlighted as will be the use of AF as a chiral building block for the preparation of other interesting compounds with biological activities such as, for example, Deoxymannojirimycin (DMJ).
[1] S.M. Andersen, I. Lundt, J. Marcussen, S. Yu, Carbohydr. Res.,337, 873 (2002).
[2] K. Bojsen, S.Yu, Shukun, K. M. Kragh, J. Marcussen, Biochimica et Biophysica Acta , 1430, 396, (1999).
[3] F.W. Lichtenthaler, E.S.H. El Ashry, V.H. Göckel, Tetrahedron Lett. 21, 1429 (1980).
Original language | English |
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Publication date | 2006 |
Publication status | Published - 2006 |
Event | 23rd International Carbohydrate Symposium - Whistler, Canada Duration: 23 Jul 2006 → 28 Jul 2006 Conference number: 23 |
Conference
Conference | 23rd International Carbohydrate Symposium |
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Number | 23 |
Country/Territory | Canada |
City | Whistler |
Period | 23/07/2006 → 28/07/2006 |