NMR analysis of novel ganglioside GM4 analogues containing de-N-acetyl and lactamized sialic acid: probes for searching new ligand structures for human L-selectin

✍ Scribed by Toshiyuki Hamada; Hiroshi Hirota; Shigeyuki Yokoyama; Nobumasa Otsubo; Hideharu Ishida; Makoto Kiso; Akiko Kanamori; Reiji Kannagi

• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: English
• Weight: 196 KB
• Volume: 40
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1048

✦ Synopsis

Abstract

Detailed analysis of the ^1^H and ^13^C NMR spectra of two novel ganglioside GM4 analogues de‐N‐acetyl sialyl GM4 (1) and cyclic sialyl GM4 (2), which contain de‐N‐acetyl and lactamized sialic acid, respectively, instead of the usual N‐acetylneuraminic acid, was carried out. The combination of NMR data, such as cyclization shifts, coupling pattern, intraresidual NOEs and the appearance of NH proton, provided the ^5, 2^B conformation for 2. Moreover, the conformation of a glycosidic bond connecting the Neu and Gal residues was determined by some interresidual NOEs in both 1 and 2. Copyright © 2002 John Wiley & Sons, Ltd.