Research & Teaching Faculty

Default Header Image

1-Deoxy-D-galactonojirimycins with dansyl capped N-substituents as beta-galactosidase inhibitors and potential probes for G(M1) gangliosidosis affected cell lines

Title1-Deoxy-D-galactonojirimycins with dansyl capped N-substituents as beta-galactosidase inhibitors and potential probes for G(M1) gangliosidosis affected cell lines
Publication TypeJournal Article
Year of Publication2011
AuthorsFroehlich, RFG, Furneaux, RH, Mahuran, DJ, Saf, R, Stuetz, AE, Tropak, MB, Wicki, J, Withers, SG, Wrodnigg, TM
JournalCARBOHYDRATE RESEARCH
Volume346
Pagination1592-1598
Date PublishedSEP 6
ISSN0008-6215
Abstract

Two simple and reliably accessible intermediates, N-carboxypentyl- and N-aminohexyl-1-deoxy-D-galactonojirimycin were employed for the synthesis of a set of terminally N-dansyl substituted derivatives. Reaction of the terminal carboxylic acid of N-carboxypentyl-1-deoxy-D-galactonojirimycin with N-dansyl-1,6-diaminohexane provided the chain-extended fluorescent derivative. Employing bis(6-dansylaminohexyl)amine, the corresponding branched di-N-dansyl compound was obtained. Partially protected N-aminohexyl-1-deoxy-D-galactonojirimycin served as intermediate for two additional chain-extended fluorescent 1-deoxy-D-galactonojirimycin (1-DGJ) derivatives featuring terminal dansyl groups in the N-alkyl substituent. These new compounds are strong inhibitors of D-galactosidases and may serve as leads en route to pharmacological chaperones for GM1-gangliosidosis. (C) 2011 Published by Elsevier Ltd.

DOI10.1016/j.carres.2011.05.010