[Synthesis of 2-acetamido-1,4-imino-1,2,4-tridesoxy-D-galactitol and competitive inhibition of human lysosomal beta-hexosaminidase A].
The synthesis of 2-acetamido-1,4-imino-1,2,4-trideoxy-D-galactitol (1; 2-acetamido-4-amino-1,4-anhydro-2,4-dideoxy-D-galactitol) by two different routes starting from 2-acetamido-2-deoxy-D-glucose is described. Compound 1 is a competitive inhibitor of human lysosomal beta-hexosaminidase A with K(i) values of 18 microM (beta-subunit) and 220 microM (alpha-subunit). Similar properties were found for the already known 2-acetamido-2-deoxy-D-gluco-hydroximo-1,4-lactone.
Liessem
B
B
Institut für Organische Chemie und Biochemie der Universität Bonn, Deutschland.
Giannis
A
A
Sandhoff
K
K
Nieger
M
M
D001667:Binding, Competitive; D004376:Galactitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006801:Humans; D050112:Imino Pyranoses; D008247:Lysosomes / Q000201:enzymology*; D008958:Models, Molecular; D015394:Molecular Structure; D001619:beta-N-Acetylhexosaminidases / Q000037:antagonists & inhibitors*
C086526:2-acetamido-1,4-imino-1,2,4-trideoxygalactitol; D050112:Imino Pyranoses; D004376:Galactitol; D001619:beta-N-Acetylhexosaminidases
Synthese von 2-Acetamido-1,4-imino-1,2,4-tridesoxy-D-galaktitol und kompetitive Inhibition der humanen lysosomalen beta-Hexosaminidase A.