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

0348116 - MBÚ 2011 RIV GB eng J - Journal Article
Catelani, G. - D’Andrea, F. - Griselli, A. - Guazelli, L. - Němcová, P. - Bezouška, K. - Křenek, Karel - Křen, Vladimír
Deoxynojirimycin and its hexosaminyl derivatives bind to natural killer cell receptors rNKR-P1A and hCD69.
Bioorganic and Medicinal Chemistry Letters. Roč. 20, č. 15 (2010), s. 4645-4648. ISSN 0960-894X. E-ISSN 1464-3405
R&D Projects: GA MŠMT OC 136; GA MŠMT(CZ) LC06010
Institutional research plan: CEZ:AV0Z50200510
Keywords : Deoxynojirimycin * NK cells * hCD69 receptors
Subject RIV: CC - Organic Chemistry
Impact factor: 2.661, year: 2010

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 disacharide intermediates
Permanent Link: http://hdl.handle.net/11104/0188728