Deoxynojirimycin (1) and two new related 4-O-hexosaminyl-containing disaccharide mimics, beta-D-Tal-NAc-(1→4)-DNJ (4) and beta-D-ManNAc-(1→4)-DNJ (5), have been studied as agonists of natural killer (NK) cell receptors. As a positive and unexpected result, DNJ (1) displayed a remarkable activation effect towards both NKR-P1A (rat) and CD69 (human) receptors, and a quite similar activity was found for 4 and 5. The synthesis of the two disaccharide mimics is based on an approach that avoids the glycosylation step using known intermediates arising from lactose. The key stage of the synthesis involves the construction of the DNJ unit through an initial C-5 oxidation of the reducing D-glucopyranosyl unit followed by a stereoselective double-reductive aminocyclization of the 1,5-dicarbonyl disaccharide intermediates.

Deoxynojirimycin and its hexosaminyl derivatives bind to natural killer cells receptors rNKR-P1A and hCD69

CATELANI, GIORGIO;D'ANDREA, FELICIA;GUAZZELLI, LORENZO;
2010

Abstract

Deoxynojirimycin (1) and two new related 4-O-hexosaminyl-containing disaccharide mimics, beta-D-Tal-NAc-(1→4)-DNJ (4) and beta-D-ManNAc-(1→4)-DNJ (5), have been studied as agonists of natural killer (NK) cell receptors. As a positive and unexpected result, DNJ (1) displayed a remarkable activation effect towards both NKR-P1A (rat) and CD69 (human) receptors, and a quite similar activity was found for 4 and 5. The synthesis of the two disaccharide mimics is based on an approach that avoids the glycosylation step using known intermediates arising from lactose. The key stage of the synthesis involves the construction of the DNJ unit through an initial C-5 oxidation of the reducing D-glucopyranosyl unit followed by a stereoselective double-reductive aminocyclization of the 1,5-dicarbonyl disaccharide intermediates.
Catelani, Giorgio; Griselli, A; D'Andrea, Felicia; Guazzelli, Lorenzo; Nemcová, P; Bezouska, B; Krenek, K; Kren, V.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/202380
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