19996-03-3Relevant academic research and scientific papers
Determination of protonation states of iminosugar-enzyme complexes using photoinduced electron transfer
Wang, Bo,Olsen, Jacob Ingemar,Laursen, Bo W.,Navarro Poulsen, Jens Christian,Bols, Mikael
, p. 7383 - 7393 (2017/10/30)
A series of N-alkylated analogues of 1-deoxynojirimycin containing a fluorescent 10-chloro-9-anthracene group in the N-alkyl substituent were prepared. The anthracene group acted as a reporting group for protonation at the nitrogen in the iminosugar because an unprotonated amine was found to quench fluorescence by photoinduced electron transfer. The new compounds were found to inhibit β-glucosidase from Phanerochaete chrysosporium and α-glucosidase from Aspergillus Niger, with Ki values in the low micro- to nanomolar range. Fluorescence and inhibition versus pH studies of the β-glucosidase-iminosugar complexes revealed that the amino group in the inhibitor is unprotonated when bound, while one of the active site carboxylates is protonated.
