Deoxynojirimycin and its hexosaminyl derivatives bind to natural killer cell receptors rNKR-P1A and hCD69
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- 作者：Giorgio Catelani ; Felicia D’ ; Andrea ; Alessio Griselli ; Lorenzo Guazzelli ; Petra Ně ; mcová ; Karel Bezouš ; ka ; Karel Kř ; enek ; Vladimí ; r Kř ; en
- 关键词：Deoxynojirimycin ; β ; -d-TalNAc-(1→ ; 4)-DNJ ; β ; -d-ManNAc-(1→ ; 4)-DNJ ; NK cells ; rNKR-P1A and hCD69 receptors
- 刊名：Bioorganic and Medicinal Chemistry Letters
- 出版年：2010
- 出版时间：1 August 2010
- 年：2010
- 卷：20
- 期：15
- 页码：4645-4648
- 全文大小：199 K
文摘
Deoxynojirimycin (1) and two new related 4-O-hexosaminyl-containing disaccharide mimics, β-d-TalNAc-(1→4)-DNJ (4) and β-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.