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A disintegrin derivative as a case study for PHIP labeling of disulfide bridged biomolecules

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. (Publisher's Version)
In: Scientific Reports, 12, Springer Nature, e-ISSN 2045-2322,
DOI: 10.26083/tuprints-00021461,
[Article]

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Item Type: Article
Origin: Secondary publication via sponsored Golden Open Access
Status: Publisher's Version
Title: A disintegrin derivative as a case study for PHIP labeling of disulfide bridged biomolecules
Language: English
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.

Journal or Publication Title: Scientific Reports
Volume of the journal: 12
Publisher: Springer Nature
Collation: 8 Seiten
Classification DDC: 500 Naturwissenschaften und Mathematik > 540 Chemie
Divisions: 07 Department of Chemistry > Organ Chemistry
07 Department of Chemistry > Physical Chemistry
Date Deposited: 07 Jun 2022 12:09
Last Modified: 07 Jun 2022 12:09
DOI: 10.26083/tuprints-00021461
Corresponding Links:
URN: urn:nbn:de:tuda-tuprints-214619
Additional Information:

Keywords: Biophysical chemistry, chemical physics, peptides

URI: https://tuprints.ulb.tu-darmstadt.de/id/eprint/21461
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