The synthetic access of either beta-D-ManNAc-(1->4)-D-Glc (5) is beta-D-TalNAc-(1->4)-D-Glc (6) disaccharides has been effectively improved with respect to previous syntheses (J. Carbohydr. Chem. 2000, 19, 79–91 and 2004, 23, 179–190), optimizing the preparation of suitably protected 4-O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-beta-D-talopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal derivatives obtained by complete stereoselective LiAlH4 reduction of new 2’-oximino precursors derived from lactose. The affinity of the disaccharides 5 and 6 toward the natural killer cell NKR-P1 and CD69 receptors has been evaluated and discussed.
Improved Preparation of beta-D-ManNAc-(1-->4)-D-Glc and beta-D-TalNAc-(1-->4)-D-Glc Disaccharides and Evaluation of Their Activating Properties on the Natural Killer Cells NKR-P1 and CD69 Receptors
CATELANI, GIORGIO;D'ANDREA, FELICIA;
2008-01-01
Abstract
The synthetic access of either beta-D-ManNAc-(1->4)-D-Glc (5) is beta-D-TalNAc-(1->4)-D-Glc (6) disaccharides has been effectively improved with respect to previous syntheses (J. Carbohydr. Chem. 2000, 19, 79–91 and 2004, 23, 179–190), optimizing the preparation of suitably protected 4-O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-beta-D-talopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal derivatives obtained by complete stereoselective LiAlH4 reduction of new 2’-oximino precursors derived from lactose. The affinity of the disaccharides 5 and 6 toward the natural killer cell NKR-P1 and CD69 receptors has been evaluated and discussed.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
