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, 12
doi: 10.1038/s41598-022-06327-z
Article, Bibliographie
This is the latest version of this item.
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.
| Item Type: | Article |
|---|---|
| Erschienen: | 2022 |
| Creators: | Fleckenstein, Max ; Herr, Kevin Sebastian ; Theiß, Franziska ; Knecht, Stephan ; Wienands, Laura ; Brodrecht, Martin ; Reggelin, Michael ; Buntkowsky, Gerd |
| Type of entry: | Bibliographie |
| Title: | A disintegrin derivative as a case study for PHIP labeling of disulfide bridged biomolecules |
| Language: | English |
| Date: | 2022 |
| Publisher: | Springer Nature |
| Journal or Publication Title: | Scientific Reports |
| Volume of the journal: | 12 |
| Collation: | 8 Seiten |
| DOI: | 10.1038/s41598-022-06327-z |
| Corresponding Links: | |
| 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. |
| Additional Information: | Keywords: Biophysical chemistry, chemical physics, peptides |
| Classification DDC: | 500 Science and mathematics > 540 Chemistry |
| Divisions: | 07 Department of Chemistry 07 Department of Chemistry > Clemens-Schöpf-Institut > Organ Chemistry 07 Department of Chemistry > Eduard Zintl-Institut > Physical Chemistry |
| Date Deposited: | 06 Dec 2023 08:41 |
| Last Modified: | 06 Dec 2023 08:41 |
| PPN: | |
| Export: | |
| Suche nach Titel in: | TUfind oder in Google |
Available Versions of this Item
-
A disintegrin derivative as a case study for PHIP labeling of disulfide bridged biomolecules. (deposited 07 Jun 2022 12:09)
- A disintegrin derivative as a case study for PHIP labeling of disulfide bridged biomolecules. (deposited 06 Dec 2023 08:41) [Currently Displayed]
 |
Send an inquiry |
Options (only for editors)
 |
Show editorial Details |
Drucken
Impressum