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Determination of protonation states of iminosugar–enzyme complexes using photoinduced electron transfer

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Abstract

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.

Graphical abstract: Determination of protonation states of iminosugar–enzyme complexes using photoinduced electron transfer

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Publication details

The article was received on 06 Apr 2017, accepted on 29 Aug 2017 and first published on 14 Sep 2017


Article type: Edge Article
DOI: 10.1039/C7SC01540B
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY-NC license
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    Determination of protonation states of iminosugar–enzyme complexes using photoinduced electron transfer

    B. Wang, J. I. Olsen, B. W. Laursen, J. C. Navarro Poulsen and M. Bols, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC01540B

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