Fleckenstein, Max ; Herr, Kevin Sebastian ; Theiß, Franziska ; Knecht, Stephan ; Wienands, Laura ; Brodrecht, Martin ; Reggelin, Michael ; Buntkowsky, Gerd (2022)
A disintegrin derivative as a case study for PHIP labeling of disulfide bridged biomolecules.
In: Scientific Reports, 2022, 12
doi: 10.26083/tuprints-00021461
Artikel, Zweitveröffentlichung, Verlagsversion
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Kurzbeschreibung (Abstract)
A specific labeling strategy for bioactive molecules is presented for eptifibatide (integrilin) an antiplatelet aggregation inhibitor, which derives from the disintegrin protein barbourin in the venom of certain rattlesnakes. By specifically labeling the disulfide bridge this molecule becomes accessible for the nuclear spin hyperpolarization method of parahydrogen induced polarization (PHIP). The PHIP-label was synthesized and inserted into the disulfide bridge of eptifibatide via reduction of the peptide and insertion by a double Michael addition under physiological conditions. This procedure is universally applicable for disulfide-containing biomolecules and preserves their tertiary structure with a minimum of change. HPLC and MS spectra prove the successful insertion of the label. 1H-PHIP-NMR experiments yield a factor of over 1000 as lower limit for the enhancement factor. These results demonstrate the high potential of the labeling strategy for the introduction of site selective PHIP-labels into biomolecules’ disulfide bonds.
| Typ des Eintrags: | Artikel |
|---|---|
| Erschienen: | 2022 |
| Autor(en): | Fleckenstein, Max ; Herr, Kevin Sebastian ; Theiß, Franziska ; Knecht, Stephan ; Wienands, Laura ; Brodrecht, Martin ; Reggelin, Michael ; Buntkowsky, Gerd |
| Art des Eintrags: | Zweitveröffentlichung |
| Titel: | A disintegrin derivative as a case study for PHIP labeling of disulfide bridged biomolecules |
| Sprache: | Englisch |
| Publikationsjahr: | 2022 |
| Publikationsdatum der Erstveröffentlichung: | 2022 |
| Verlag: | Springer Nature |
| Titel der Zeitschrift, Zeitung oder Schriftenreihe: | Scientific Reports |
| Jahrgang/Volume einer Zeitschrift: | 12 |
| Kollation: | 8 Seiten |
| DOI: | 10.26083/tuprints-00021461 |
| URL / URN: | https://tuprints.ulb.tu-darmstadt.de/21461 |
| Zugehörige Links: | |
| Herkunft: | Zweitveröffentlichung aus gefördertem Golden Open Access |
| Kurzbeschreibung (Abstract): | A specific labeling strategy for bioactive molecules is presented for eptifibatide (integrilin) an antiplatelet aggregation inhibitor, which derives from the disintegrin protein barbourin in the venom of certain rattlesnakes. By specifically labeling the disulfide bridge this molecule becomes accessible for the nuclear spin hyperpolarization method of parahydrogen induced polarization (PHIP). The PHIP-label was synthesized and inserted into the disulfide bridge of eptifibatide via reduction of the peptide and insertion by a double Michael addition under physiological conditions. This procedure is universally applicable for disulfide-containing biomolecules and preserves their tertiary structure with a minimum of change. HPLC and MS spectra prove the successful insertion of the label. 1H-PHIP-NMR experiments yield a factor of over 1000 as lower limit for the enhancement factor. These results demonstrate the high potential of the labeling strategy for the introduction of site selective PHIP-labels into biomolecules’ disulfide bonds. |
| Status: | Verlagsversion |
| URN: | urn:nbn:de:tuda-tuprints-214619 |
| Zusätzliche Informationen: | Keywords: Biophysical chemistry, chemical physics, peptides |
| Sachgruppe der Dewey Dezimalklassifikatin (DDC): | 500 Naturwissenschaften und Mathematik > 540 Chemie |
| Fachbereich(e)/-gebiet(e): | 07 Fachbereich Chemie 07 Fachbereich Chemie > Clemens-Schöpf-Institut > Fachgebiet Organische Chemie 07 Fachbereich Chemie > Eduard Zintl-Institut > Fachgebiet Physikalische Chemie |
| Hinterlegungsdatum: | 07 Jun 2022 12:09 |
| Letzte Änderung: | 06 Dez 2023 08:41 |
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| Suche nach Titel in: | TUfind oder in Google |
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- A disintegrin derivative as a case study for PHIP labeling of disulfide bridged biomolecules. (deposited 07 Jun 2022 12:09) [Gegenwärtig angezeigt]
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