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Department of Pharmaceutical Analysis, University of Sarajevo, Faculty of Pharmacy, Zmaja od Bosne 8, Sarajevo, 71 000, Bosnia and Herzegovina
Department of Medical Chemistry, University of Szeged, Faculty of Medicine, 8 Dóm tér, Szeged, 6720, Hungary
MTA-SZTE Biomimetic Systems Research Group, University of Szeged, Dóm tér 8, Szeged, 6720, Hungary
Cited By :2
Export Date: 8 September 2023
CODEN: CBCHF
Correspondence Address: Hegedüs, Z.; Department of Medical Chemistry, 8 Dóm tér, Hungary; email: hegedus.zsofia@med.u-szeged.hu
Correspondence Address: Martinek, T.A.; Department of Medical Chemistry, 8 Dóm tér, Hungary; email: martinek.tamas@med.u-szeged.hu
Correspondence Address: Martinek, T.A.; MTA-SZTE Biomimetic Systems Research Group, Dóm tér 8, Hungary; email: martinek.tamas@med.u-szeged.hu
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DPP-4 Cleaves alpha/beta-Peptide Bonds: Substrate Specificity and Half-Lives
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The incorporation of beta-amino acids into a peptide sequence has gained particular attention as beta- and alpha/beta-peptides have shown remarkable proteolytic stability, even after a single homologation at the scissile bond. Several peptidases have been shown to cleave such bonds with high specificity but at a much slower rate compared to alpha-peptide bonds. In this study, a series of analogs of dipeptidyl peptidase-4 (DPP-4) substrate inhibitors were synthesized in order to investigate whether beta-amino acid homologation at the scissile bond could be a valid approach to improving peptide stability towards DPP-4 degradation. DPP-4 cleaved the alpha/beta-peptide bond after the N-terminal penultimate Pro with a broad specificity and retained full activity regardless of the beta(3)-amino acid side chain and peptide length. Significantly improved half-lives were observed for beta(3)Ile-containing peptides. Replacing the penultimate Pro with a conformationally constrained Pro mimetic led to proteolytic resistance. DPP-4 cleavage of alpha/beta-peptide bonds with a broad promiscuity represents a new insight into the stability of peptide analogs containing beta-amino acids as such analogs were thought to be stable towards enzymatic degradation.
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" > Turalic, Amila </span> <span class="author-type"> </span> ; <span class="author-name" > Dedibegovic, Jasmina </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10043382"> <a href="/gui2/?type=authors&mode=browse&sel=10043382" target="_blank">Hegedus, Zsofia ✉</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10001168"> <a href="/gui2/?type=authors&mode=browse&sel=10001168" target="_blank">Martinek, Tamas A. ✉</a> </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;31371344" mtid="31371344" target="_blank">DPP-4 Cleaves alpha/beta-Peptide Bonds: Substrate Specificity and Half-Lives</a></div> <div class="pub-info"> <span class="journal-title">CHEMBIOCHEM</span> <span class="journal-volume">21</span> : <span class="journal-issue">14</span> <span class="page"> pp. 2060-2066. , 7 p. </span> <span class="year">(2020)</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_PAY" title=" Fizetős "> <a style="color:blue" title="10.1002/cbic.202000050" target="_blank" href="https://doi.org/10.1002/cbic.202000050"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000522535500001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000522535500001"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85082747339" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85082747339"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:black" title="32180303" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=32180303&dopt=Abstract"> PubMed </a> </span> <span class="id identifier oa_GREEN" title=" Green "> <a style="color:blue" title="22614" target="_blank" href="http://publicatio.bibl.u-szeged.hu/22614"> SZTE Publicatio </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:31371344 </span> <span class="status-holder"><span class="status-data status-VALIDATED"> Egyeztetett </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Folyóiratcikk (Szakcikk ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> <div class="publication-citation" style="margin-left: 0.5cm;"> <span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 2</span> | Független: 2 | Függő: 0 | Nem jelölt: 0 | WoS jelölt: 2 | Scopus jelölt: 2 | WoS/Scopus jelölt: 2 | DOI jelölt: 2 </div> </div> </div> </div><div class="JournalArticle Publication long-list">
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<div class="title"><a href="/gui2/?mode=browse¶ms=publication;31371344" target="_blank">DPP-4 Cleaves alpha/beta-Peptide Bonds: Substrate Specificity and Half-Lives</a></div> <div> <span class="journal-title">CHEMBIOCHEM</span>
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<div class="mtid"><span class="long-pub-mtid">Közlemény: 31371344</span>
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Forrás Idéző
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<div class="lastModified">Utolsó módosítás: 2022.10.11. 14:02 MTMT API (MTMT API user, admin)
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<pre class="comment" style="margin-top: 0; margin-bottom: 0;"><u>Megjegyzés</u>: Department of Pharmaceutical Analysis, University of Sarajevo, Faculty of Pharmacy, Zmaja od Bosne 8, Sarajevo, 71 000, Bosnia and Herzegovina
Department of Medical Chemistry, University of Szeged, Faculty of Medicine, 8 Dóm tér, Szeged, 6720, Hungary
MTA-SZTE Biomimetic Systems Research Group, University of Szeged, Dóm tér 8, Szeged, 6720, Hungar...</pre>
</div></div>