Spacer-modified disaccharide and pseudo-trisaccharide methyl glycosides that mimic maltotriose, as competitive inhibitors for pancreatic alpha-amylase: a demonstration of the "clustering effect"

Carbohydr Res. 1992 Feb 7:224:59-71. doi: 10.1016/0008-6215(92)84093-8.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • Disaccharides / chemistry
  • Molecular Sequence Data
  • Pancreas / enzymology*
  • Thioglycosides / chemical synthesis
  • Thioglycosides / metabolism*
  • Trisaccharides / chemistry
  • alpha-Amylases / antagonists & inhibitors*

Substances

  • Disaccharides
  • Thioglycosides
  • Trisaccharides
  • maltotriose
  • alpha-Amylases