The solution conformation of acarbose

✍ Scribed by Klaus Bock; Henrik Pedersen

• Publisher: Elsevier Science
• Year: 1984
• Tongue: English
• Weight: 388 KB
• Volume: 132
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(84)85072-7

✦ Synopsis

The pseudotetrasaccharide acarbose (1) is a potent inhibitor of glucosidases and saccharases in in vitro systems'%*, and is of potential interest in connection with the regulation of the uptake of D-glUCOSe in the intestine. In order to obtain a better understanding of the inhibitory activity of 1, we have investigated its solution conformation using, particularly, 'H-n.m.r. spectroscopy and proton n.0.e. in combination with an empirical evaluation of the preferred conformation using the hardspheres exe-anomeric effect (HSEA) calculation". This method has given convincing results about the preferred conformation of oligosaccharides in solution4-9.

The 'H-n.m.r. data (400 or 500 MHz) for 1 and the disaccharide glycoside 2 are presented in Table I, and a spectrum of 1 in aqueous solution is shown in Fig. 1. The assignments of the signals given in Table I are based on comparison with those of appropriate model compounds'", homonuclear decoupling experiments, and partially relaxed spectra. The '3C-n.m.r. data (67.89 MHz) of 1 and 2 are shown in Table II. The assignments of these signals were based on comparison with those of suitable model compounds".