SYNTHESIS OF SIALYL- AND SULFO-Le^x/Le^a ANALOGS CONTAINING N-ALKYL-1-DEOXYNOJIRIMYCIN AS POTENTIAL SELECTIN BLOCKERS[1]

Abstract

A series of novel sialyl- and sulfo-Le^x/Le^a oligosaccharides containing N-alkyl-1-deoxynojirimycin as potential selectin blockers have systematically been synthesized via the suitably protected intermediates containing N-benzyloxycarbonyl-1-deoxynojirimycin. Some of the synthetic oligosaccharides strongly inhibited the adhesion of HL60 cells to IL-1β-stimulated HUVECs.

ACKNOWLEDGMENTS

This work was supported in part by Grants-in-Aid for Scientific Research from the Ministry of Education, Science, and Culture of Japan. The authors thank Dr. Takao Ikami of Sanwa Kagaku Kenkyusho for FAB-MS measurements, Dr. Akihiro Kondo of Biotechnology Research Laboratories, Takara Shuzo Co., Ltd. for the ion-spray MS analysis, and Drs. Yohji Ezure, Yoshiaki Yoshikuni, and Tadaaki Ohgi of Nippon Shinyaku Co., Ltd. for multiform support including selectin binding assay.