| Title | 1-Deoxy-d-galactonojirimycins with dansyl capped N-substituents as β-galactosidase inhibitors and potential probes for GM1 gangliosidosis affected cell lines |
| Publication Type | Journal Article |
| Year of Publication | 2011 |
| Authors | Fröhlich, R. F. G., Furneaux R. H., Mahuran D. J., Saf R., Stütz A. E., Tropak M. B., Wicki J., Withers S. G., and Wrodnigg T. M. |
| IRL Team | Carbohydrate Chemistry |
| Journal | Carbohydrate Research |
| Volume | 346 |
| Pagination | 1592-1598 |
| Keywords | 4 o isopropylidene 1, 5 dideoxy 1, 5 imino dextro galactitol, 6 diaminohexane, alkylation, animal cell, article, beta galactosidase, beta glucosidase, Carboxylic acids, Cell culture, chaperone, drug structure, enzyme activity, enzyme inhibition, fibroblast, Fluorescence, fluorescent dye, Galactosidases, glycosidase inhibitor, GM1 gangliosidosis, GM1-gangliosidosis, human, human cell, Iminoalditol, Molecular chaperone, n (dansylamino)hexylaminocarbonylpentyl 1, n (dansylaminohexylamino)hexyl 3, n aminohexyl 1 deoxy dextro galactonojirimycin, n bis(dansylaminohexyl)aminocarbonylpentyl 1, n bis(dansylaminohexyl)aminohexyl 1, n bis(dansylaminohexyl)aminohexyl 3, n carboxypentyl 1 deoxy dextro galactonojirimycin, n dansyl 1, n [(dansylaminohexyl) n octanoylamino]hexyl 1, n [(dansylaminohexyl) n octanoylamino]hexyl 3, N-alkylation, nonhuman, priority journal, substitution reaction, Synthesis (chemical), unclassified drug |
| 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. © 2011 Elsevier Ltd. All rights reserved. |
| URL | http://www.scopus.com/inward/record.url?eid=2-s2.0-79959980422&partnerID=40&md5=80fe5b6d9173e51e83b0e3aa66ad09e9 |
| DOI | 10.1016/j.carres.2011.05.010 |
