Spacer-modified disaccharide and pseudo-trisaccharide methyl glycosides that mimic maltotriose, as competitive inhibitors for pancreatic alpha-amylase: a demonstration of the "clustering effect".
The synthesis is reported of methyl 4,4'-dithio-alpha-maltotrioside (12) and the spacer-modified disaccharide glycosides methyl 4-S-(4-alpha-D-glucopyranosylthio-2-hydroxybutyl)-4-thio-alpha -D-glucopyranoside (20) and methyl 4-S-[(1,5/4,6)- and (4,6/1,5)-4-alpha-D-glucopyranosylthio-5,6-dihydroxy-2- cyclohexen-1-yl]-4-thio-alpha-D-glucopyranoside (29a/b), which are analogues of methyl alpha-maltotrioside. The Ki values for alpha-amylase for these compounds were determined as were those of methyl alpha-maltotrioside and maltose.
Blanc-Muesser
M
M
Centre de Recherches sur les Macromolecules Vegetales C.N.R.S., Grenoble, France.
Vigne
L
L
Driguez
H
H
Lehmann
J
J
Steck
J
J
Urbahns
K
K
D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000737:chemistry; D008969:Molecular Sequence Data; D010179:Pancreas / Q000201:enzymology*; D013865:Thioglycosides / Q000138:chemical synthesis / Q000378:metabolism*; D014312:Trisaccharides / Q000737:chemistry; D000516:alpha-Amylases / Q000037:antagonists & inhibitors*
D004187:Disaccharides; D013865:Thioglycosides; D014312:Trisaccharides; C008317:maltotriose; D000516:alpha-Amylases