1,5-Anhydro-D-fructose (AF) is a valuable chiral building block[1,2] which is available by degradation from starch by a-1,4-glucan lyase and which now also can be produced by efficient synthetic proedures. AF has three different functional hydroxyl groups, a pro-chiral center and a permanent pyran ring thus making selective manipulations possible. In the present work methods for stereoselective amino functionalisation at C-2 has been developed to give 2-amino-2-deoxy-1,5-anhydroalditols with manno- and gluco-configuration, respectively. The 2-acetamido-2-deoxy-1,5-anhydroglucitol has been shown to cause feeding suppression. An efficient synthesis of the important glycosidase inhibitor deoxymannojirimycin (DMJ) from AF has been achieved. Acetylation of AF gives the unsaturated ketone[2,4] which was used for preparation of the natural product Clavulazine as well as the valuable antioxidant Ascopyrone P.  S. M. Andersen, I. Lundt, J. Marcussen and S.Yu, Carbohydr. Res. 337, 873 (2002).  EU-program NEPSA (NEw Products from Starch derived Anhydro-D-fructose) under the Cell Factory of 5th Framework Program, QLK3-2001-02400  I. Lundt, M. Andreassen and A. Stütz, PA 2004 01060  O. Deppe, A. Glümer, K. Bucholtz, S. Yu, Carbohydr. Res. 339, 2077 (2004).
|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|