Novel O-glycosyl amino acid mimetics as building blocks for O-glycopeptides act as inhibitors of galactosidases.
As potential lead structures for a new class of glycosidase inhibitors the novel O-glycosyl amino acid mimetics 3'-O-[2,6-anhydro-D-glycero-L-gluco-heptitol-1-yl]-L-serine 3 and-L-threonine 4 were synthesized, employing regio- and stereoselective aziridine ring opening methodology. They proved to be stable in the presence of glycosidases and showed competitive inhibition of alpha-galactosidase from Aspergillus niger.
Kröger
Lars
L
Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, Hamburg, Germany.
Henkensmeier
Dirk
D
Schäfer
Andreas
A
Thiem
Joachim
J
D000596:Amino Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D005696:Galactosidases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D006020:Glycopeptides / Q000737:chemistry* / Q000494:pharmacology; D006027:Glycosides / Q000138:chemical synthesis*; D018716:Molecular Mimicry
D000596:Amino Acids; D004791:Enzyme Inhibitors; D006020:Glycopeptides; D006027:Glycosides; D005696:Galactosidases