Synthesis of 5a-carba-hexopyranoses and hexopyranosylamines, as well as 5a,5a'-dicarbadisaccharides, from 3,8-dioxatricyclo[4.2.1.0(2,4)]nonan-9-ol: glycosidase inhibitory activity of N-substituted 5a-carba-beta-gluco- and beta-galactopyranosylamines, and derivatives thereof.
Since glycosidase and glycosyltransferase inhibitors, composed of carba-sugars, have recently attracted much attention, it is desirable to develop effective preparative routes for provision of new carba-sugar derivatives of potential biological interest. 1,2:3,6-Dianhydro-5a-carba-alpha-glucopyranose was here chosen for study of synthetic utility, and demonstrated to be a promising intermediate for supplying several carba-beta-glycosylamines and N-linked dicarba-oligosaccharides. An N-linked 5a,5a'-dicarbalactose derivative obtained here was found to be a strong alpha-galactosidase inhibitor (IC50 1.2 microM, green coffee beans).
Ogawa
Seiichiro
S
Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. ogawa@bio.keio.ac.jp
Funayama
Sho
S
Okazaki
Kensuke
K
Ishizuka
Fumito
F
Sakata
Yoko
Y
Doi
Fuminao
F
D000473:Alkanes / Q000737:chemistry*; D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D005690:Galactose / Q000138:chemical synthesis* / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*
D000473:Alkanes; D000606:Amino Sugars; D004187:Disaccharides; D006575:Heterocyclic Compounds, 3-Ring; D006026:Glycoside Hydrolases; D005690:Galactose