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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Email: bols@chem.ku.dk ; Tel: +45 35320160.</nlm:affiliation><wicri:noCountry code="subField">Denmark </wicri:noCountry></affiliation></author><author><name sortKey="Laursen, Bo W" sort="Laursen, Bo W" uniqKey="Laursen B" first="Bo W" last="Laursen">Bo W. Laursen</name><affiliation><nlm:affiliation>Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark . Email: bols@chem.ku.dk ; Tel: +45 35320160.</nlm:affiliation><wicri:noCountry code="subField">Denmark </wicri:noCountry></affiliation></author><author><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><affiliation><nlm:affiliation>Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark . Email: bols@chem.ku.dk ; Tel: +45 35320160.</nlm:affiliation><wicri:noCountry code="subField">Denmark </wicri:noCountry></affiliation></author><author><name sortKey="Bols, Mikael" sort="Bols, Mikael" uniqKey="Bols M" first="Mikael" last="Bols">Mikael Bols</name><affiliation><nlm:affiliation>Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark . Email: bols@chem.ku.dk ; Tel: +45 35320160.</nlm:affiliation><wicri:noCountry code="subField">Denmark </wicri:noCountry></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2017">2017</date><idno type="RBID">pubmed:29163889</idno><idno type="pmid">29163889</idno><idno type="doi">10.1039/c7sc01540b</idno><idno type="pmc">PMC5672842</idno><idno type="wicri:Area/Main/Corpus">000141</idno><idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Corpus" wicri:corpus="PubMed">000141</idno><idno type="wicri:Area/Main/Curation">000141</idno><idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Curation">000141</idno><idno type="wicri:Area/Main/Exploration">000141</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Determination of protonation states of iminosugar-enzyme complexes using photoinduced electron transfer.</title><author><name sortKey="Wang, Bo" sort="Wang, Bo" uniqKey="Wang B" first="Bo" last="Wang">Bo Wang</name><affiliation><nlm:affiliation>Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark . Email: bols@chem.ku.dk ; Tel: +45 35320160.</nlm:affiliation><wicri:noCountry code="subField">Denmark </wicri:noCountry></affiliation></author><author><name sortKey="Olsen, Jacob Ingemar" sort="Olsen, Jacob Ingemar" uniqKey="Olsen J" first="Jacob Ingemar" last="Olsen">Jacob Ingemar Olsen</name><affiliation><nlm:affiliation>Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark . Email: bols@chem.ku.dk ; Tel: +45 35320160.</nlm:affiliation><wicri:noCountry code="subField">Denmark </wicri:noCountry></affiliation></author><author><name sortKey="Laursen, Bo W" sort="Laursen, Bo W" uniqKey="Laursen B" first="Bo W" last="Laursen">Bo W. Laursen</name><affiliation><nlm:affiliation>Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark . Email: bols@chem.ku.dk ; Tel: +45 35320160.</nlm:affiliation><wicri:noCountry code="subField">Denmark </wicri:noCountry></affiliation></author><author><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><affiliation><nlm:affiliation>Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark . Email: bols@chem.ku.dk ; Tel: +45 35320160.</nlm:affiliation><wicri:noCountry code="subField">Denmark </wicri:noCountry></affiliation></author><author><name sortKey="Bols, Mikael" sort="Bols, Mikael" uniqKey="Bols M" first="Mikael" last="Bols">Mikael Bols</name><affiliation><nlm:affiliation>Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark . Email: bols@chem.ku.dk ; Tel: +45 35320160.</nlm:affiliation><wicri:noCountry code="subField">Denmark </wicri:noCountry></affiliation></author></analytic><series><title level="j">Chemical science</title><idno type="ISSN">2041-6520</idno><imprint><date when="2017" type="published">2017</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><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></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">29163889</PMID><DateRevised><Year>2020</Year><Month>09</Month><Day>29</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Print">2041-6520</ISSN><JournalIssue CitedMedium="Print"><Volume>8</Volume><Issue>11</Issue><PubDate><Year>2017</Year><Month>Nov</Month><Day>01</Day></PubDate></JournalIssue><Title>Chemical science</Title><ISOAbbreviation>Chem Sci</ISOAbbreviation></Journal><ArticleTitle>Determination of protonation states of iminosugar-enzyme complexes using photoinduced electron transfer.</ArticleTitle><Pagination><MedlinePgn>7383-7393</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1039/c7sc01540b</ELocationID><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></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Wang</LastName><ForeName>Bo</ForeName><Initials>B</Initials><Identifier Source="ORCID">0000-0001-8013-1403</Identifier><AffiliationInfo><Affiliation>Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark . Email: bols@chem.ku.dk ; Tel: +45 35320160.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Olsen</LastName><ForeName>Jacob Ingemar</ForeName><Initials>JI</Initials><Identifier Source="ORCID">0000-0002-3690-6459</Identifier><AffiliationInfo><Affiliation>Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark . Email: bols@chem.ku.dk ; Tel: +45 35320160.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Laursen</LastName><ForeName>Bo W</ForeName><Initials>BW</Initials><Identifier Source="ORCID">0000-0002-1120-3191</Identifier><AffiliationInfo><Affiliation>Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark . Email: bols@chem.ku.dk ; Tel: +45 35320160.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Navarro Poulsen</LastName><ForeName>Jens Christian</ForeName><Initials>JC</Initials><Identifier Source="ORCID">0000-0002-3553-0015</Identifier><AffiliationInfo><Affiliation>Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark . Email: bols@chem.ku.dk ; Tel: +45 35320160.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Bols</LastName><ForeName>Mikael</ForeName><Initials>M</Initials><Identifier Source="ORCID">0000-0002-6561-6952</Identifier><AffiliationInfo><Affiliation>Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark . 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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></noCountry></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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