1,5-Anhydro-D-fructose (AF) is a valuable chiral building block for organic synthesis. However, the antioxidant and antimicrobial properties of AF are equally important. 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  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. 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).  S.M. Andersen, I. Lundt, J. Marcussen, S. Yu, Carbohydr. Res.,337, 873 (2002).  K. Bojsen, S.Yu, Shukun, K. M. Kragh, J. Marcussen, Biochimica et Biophysica Acta , 1430, 396, (1999).  F.W. Lichtenthaler, E.S.H. El Ashry, V.H. Göckel, Tetrahedron Lett. 21, 1429 (1980).
|Publication status||Published - 2006|
|Event||23rd International Carbohydrate Symposium - Whistler, Canada|
Duration: 23 Jul 2006 → 28 Jul 2006
Conference number: 23
|Conference||23rd International Carbohydrate Symposium|
|Period||23/07/2006 → 28/07/2006|