Beilstein J. Org. Chem.2010,6, No. 21, doi:10.3762/bjoc.6.21
related β-galactosidase mutants.
Keywords: chemical chaperones; 1-deoxy-D-galactonojirimycin; iminosugars; lipophilic galactosidase inhibitor; N-modified iminosugars; Introduction
Iminosugars such as compounds 1–4 (Figure 1) have been shown to be potent glycosidase inhibitors and useful tools for the
neurological deterioration [23].
Our studies revealed that 1-deoxy-D-galactonojirimycin-lysine hybrids, when carrying an aromatic substituent, such as a dansyl moiety, in its nature a lipophilic aromatic substituent, are potent D-galactosidase inhibitors and also show activity with human lysosomal β
step after brief silica gel purification. The reductive amination and N-deprotection of 11 was carried out under an atmosphere of H2 with benzylamine in methanol and Pd/C as catalyst to produce 3,4-O-isopropylidene-1-deoxy-D-galactonojirimycin (12) in an overall yield of 75% (Scheme 1).
Compound 12