Improved Preparation of β-d-ManNAc-(1→4)-d-Glc and β-d-TalNAc-(1→4)-d-Glc Disaccharides and Evaluation of Their Activating Properties on the Natural Killer Cells NKR-P1 and CD69 Receptors
Titel:
Improved Preparation of β-d-ManNAc-(1→4)-d-Glc and β-d-TalNAc-(1→4)-d-Glc Disaccharides and Evaluation of Their Activating Properties on the Natural Killer Cells NKR-P1 and CD69 Receptors
Auteur:
Attolino, Emanuele Bonaccorsi, Filippo Catelani, Giorgio D'Andrea, Felicia Krenek, Karel Bezouska, Karel Kren, Vladimir
Verschenen in:
Journal of carbohydrate chemistry
Paginering:
Jaargang 27 (2008) nr. 3 pagina's 156-171
Jaar:
2008-03
Inhoud:
The synthetic access of either β-d-ManNAc-(1→4)-d-Glc (5) is β-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-β-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.