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Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors.

ABSTRACT: N-Alkylation at the ring nitrogen of the D-galactosidase inhibitor 1-deoxygalactonojirimycin with a functionalised C ?alkyl chain followed by modification with different aromatic substituents provided lipophilic 1-deoxygalactonojirimycin derivatives which exhibit inhibitory properties against ?-glycosidases from E. coli and Agrobacterium sp. as well as green coffee bean ?-galactosidase. In preliminary studies, these compounds also showed potential as chemical chaperones for GM1-gangliosidosis related ?-galactosidase mutants.

SUBMITTER: Schitter G

PROVIDER: S-EPMC2874416 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors.

Schitter Georg G Scheucher Elisabeth E Steiner Andreas J AJ Stütz Arnold E AE Thonhofer Martin M Tarling Chris A CA Withers Stephen G SG Wicki Jacqueline J Fantur Katrin K Paschke Eduard E Mahuran Don J DJ Rigat Brigitte A BA Tropak Michael M Wrodnigg Tanja M TM

Beilstein journal of organic chemistry 20100301

N-Alkylation at the ring nitrogen of the D-galactosidase inhibitor 1-deoxygalactonojirimycin with a functionalised C ₆alkyl chain followed by modification with different aromatic substituents provided lipophilic 1-deoxygalactonojirimycin derivatives which exhibit inhibitory properties against β-glycosidases from E. coli and Agrobacterium sp. as well as green coffee bean α-galactosidase. In preliminary studies, these compounds also showed potential as chemical chaperones for GM1-gangliosidosis re ...[more]

PMID: 20502610

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