Synthesis and enzyme-inhibitory activity of methyl acarviosin analogues having the alpha-manno configuration.
Two methyl acarviosin analogues 3a and 4a, having the alpha-manno configuration, and their dihydro derivatives 6a and 7a were synthesised by coupling the protected pseudo-sugar epoxides with methyl 4-amino-4-deoxy- and -4,6-dideoxy-alpha-D-mannopyranoside. Similarly, two analogous compounds 5a and 8a composed of the 1,6-anhydro-beta-D-mannopyranose residues were prepared. Compound 7a showed mild inhibitory activity against Jack bean alpha-D-mannosidase, and 3a was a moderate inhibitor of both alpha-D-mannosidase and yeast alpha-D-glucosidase.
Ogawa
S
S
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.
Nakamura
Y
Y
D000606:Amino Sugars / Q000737:chemistry / Q000494:pharmacology*; D002240:Carbohydrate Sequence; D065089:Glycoside Hydrolase Inhibitors; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D008320:Maltose / Q000031:analogs & derivatives; D008361:Mannosidases / Q000037:antagonists & inhibitors; D008969:Molecular Sequence Data; D013237:Stereoisomerism; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors
D000606:Amino Sugars; D065089:Glycoside Hydrolase Inhibitors; D008320:Maltose; D006026:Glycoside Hydrolases; D008361:Mannosidases; D001617:beta-Glucosidase