Determination of protonation states of iminosugar-enzyme complexes using photoinduced electron transfer.
Identifieur interne : 000177 ( Main/Exploration ); précédent : 000176; suivant : 000178Determination of protonation states of iminosugar-enzyme complexes using photoinduced electron transfer.
Auteurs : Bo Wang ; Jacob Ingemar Olsen ; Bo W. Laursen ; Jens Christian Navarro Poulsen ; Mikael BolsSource :
- Chemical science [ 2041-6520 ] ; 2017.
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.
DOI: 10.1039/c7sc01540b
PubMed: 29163889
PubMed Central: PMC5672842
Affiliations:
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<front><div type="abstract" xml:lang="en">A series of <i>N</i>
-alkylated analogues of 1-deoxynojirimycin containing a fluorescent 10-chloro-9-anthracene group in the <i>N</i>
-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 <i>Phanerochaete chrysosporium</i>
and α-glucosidase from <i>Aspergillus niger</i>
, with <i>K</i>
<sub>i</sub>
values in the low micro- to nanomolar range. Fluorescence and inhibition <i>versus</i>
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.</div>
</front>
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<ArticleTitle>Determination of protonation states of iminosugar-enzyme complexes using photoinduced electron transfer.</ArticleTitle>
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<Abstract><AbstractText>A series of <i>N</i>
-alkylated analogues of 1-deoxynojirimycin containing a fluorescent 10-chloro-9-anthracene group in the <i>N</i>
-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 <i>Phanerochaete chrysosporium</i>
and α-glucosidase from <i>Aspergillus niger</i>
, with <i>K</i>
<sub>i</sub>
values in the low micro- to nanomolar range. Fluorescence and inhibition <i>versus</i>
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.</AbstractText>
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<name sortKey="Laursen, Bo W" sort="Laursen, Bo W" uniqKey="Laursen B" first="Bo W" last="Laursen">Bo W. Laursen</name>
<name sortKey="Navarro Poulsen, Jens Christian" sort="Navarro Poulsen, Jens Christian" uniqKey="Navarro Poulsen J" first="Jens Christian" last="Navarro Poulsen">Jens Christian Navarro Poulsen</name>
<name sortKey="Olsen, Jacob Ingemar" sort="Olsen, Jacob Ingemar" uniqKey="Olsen J" first="Jacob Ingemar" last="Olsen">Jacob Ingemar Olsen</name>
<name sortKey="Wang, Bo" sort="Wang, Bo" uniqKey="Wang B" first="Bo" last="Wang">Bo Wang</name>
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