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<export-example>
  <doc>
    <id>54998</id>
    <completedYear/>
    <publishedYear>2022</publishedYear>
    <thesisYearAccepted/>
    <language>eng</language>
    <pageFirst>1</pageFirst>
    <pageLast>6</pageLast>
    <pageNumber/>
    <edition/>
    <issue>25</issue>
    <volume>134</volume>
    <type>article</type>
    <publisherName>Wiley-VCH GmbH</publisherName>
    <publisherPlace/>
    <creatingCorporation/>
    <contributingCorporation/>
    <belongsToBibliography>1</belongsToBibliography>
    <completedDate>--</completedDate>
    <publishedDate>--</publishedDate>
    <thesisDateAccepted>--</thesisDateAccepted>
    <title language="eng">Pentafluorophosphato-Phenylalanines: Amphiphilic Phosphotyrosine Mimetics Displaying Fluorine-Specific Protein Interactions</title>
    <abstract language="eng">Phosphotyrosine residues are essential functional switches in health and disease. Thus, phosphotyrosine biomimetics are crucial for the development of chemical tools and drug molecules. We report here the discovery and investigation of pentafluorophosphato amino acids as novel phosphotyrosine biomimetics. A mild acidic pentafluorination protocol was developed and two PF5-amino acids were prepared and employed in peptide synthesis. Their structures, reactivities, and fluorine-specific interactions were studied by NMR and IR spectroscopy, X-ray diffraction, and in bioactivity assays. The mono-anionic PF5 motif displayed an amphiphilic character binding to hydrophobic surfaces, to water molecules, and to protein-binding sites, exploiting charge and H−F-bonding interactions. The novel motifs bind 25- to 30-fold stronger to the phosphotyrosine binding site of the protein tyrosine phosphatase PTP1B than the best current biomimetics, as rationalized by computational methods, including molecular dynamics simulations.</abstract>
    <parentTitle language="eng">Angewandte Chemie International Edition</parentTitle>
    <identifier type="doi">10.1002/anie.202203579</identifier>
    <identifier type="issn">1433-7851</identifier>
    <identifier type="urn">urn:nbn:de:kobv:b43-549984</identifier>
    <enrichment key="opus.source">publish</enrichment>
    <enrichment key="date_peer_review">13.06.2022</enrichment>
    <enrichment key="opus.doi.autoCreate">false</enrichment>
    <enrichment key="opus.urn.autoCreate">true</enrichment>
    <licence>Creative Commons - CC BY-NC - Namensnennung - Nicht kommerziell 4.0 International</licence>
    <author>M. Accorsi</author>
    <author>M. Tiemann</author>
    <author>L. Wehrhan</author>
    <author>Lauren M. Finn</author>
    <author>R. Cruz</author>
    <author>Max Rautenberg</author>
    <author>Franziska Emmerling</author>
    <author>J. Heberle</author>
    <author>B. G. Keller</author>
    <author>J. Rademann</author>
    <subject>
      <language>eng</language>
      <type>uncontrolled</type>
      <value>Chemical Biology</value>
    </subject>
    <subject>
      <language>eng</language>
      <type>uncontrolled</type>
      <value>Drug Development</value>
    </subject>
    <subject>
      <language>eng</language>
      <type>uncontrolled</type>
      <value>Pentafluorophosphates</value>
    </subject>
    <subject>
      <language>eng</language>
      <type>uncontrolled</type>
      <value>Phosphotyrosine Biomimetics</value>
    </subject>
    <subject>
      <language>eng</language>
      <type>uncontrolled</type>
      <value>Protein Tyrosine Phosphatases</value>
    </subject>
    <collection role="ddc" number="543">Analytische Chemie</collection>
    <collection role="institutes" number="">6 Materialchemie</collection>
    <collection role="institutes" number="">6.3 Strukturanalytik</collection>
    <collection role="themenfelder" number="">Chemie und Prozesstechnik</collection>
    <collection role="literaturgattung" number="">Verlagsliteratur</collection>
    <collection role="fulltextaccess" number="">Datei für die Öffentlichkeit verfügbar ("Open Access")</collection>
    <collection role="unnumberedseries" number="">Wissenschaftliche Artikel der BAM</collection>
    <collection role="institutes" number="">6.0 Abteilungsleitung und andere</collection>
    <thesisPublisher>Bundesanstalt für Materialforschung und -prüfung (BAM)</thesisPublisher>
    <file>https://opus4.kobv.de/opus4-bam/files/54998/Accorsi_Angew Chem_2022_Pentafluorophosphato-Phenylalanin.pdf</file>
  </doc>
</export-example>
