Reaction behaviour of peptide-based single thiol-thioesters exchange reaction substrate in the presence of externally added thiols
- Identification of patterns in chemical reaction pathways aids in the effective design of molecules for specific applications. Here, we report on model reactions with a water-soluble single thiol-thioester exchange (TTE) reaction substrate, which was designed taking in view biological and medical applications. This substrate consists of the thio-depsipeptide, Ac-Pro-Leu-Gly-SLeu-Leu-Gly-NEtSH (TDP) and does not yield foul-smelling thiol exchange products when compared with aromatic thiol containing single TTE substrates. TDP generates an alpha,omega-dithiol crosslinker in situ in a 'pseudo intramolecular' TTE. Competitive intermolecular TTE of TDP with externally added "basic" thiols increased the crosslinker concentration whilst "acidic" thiols decreased its concentration. TDP could potentially enable in situ bioconjugation and crosslinking applications.
| Verfasserangaben: | Makafui Y. FolikumahORCiDGND, Marc BehlORCiDGND, Andreas LendleinORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1557/s43579-021-00041-z |
| ISSN: | 2159-6859 |
| ISSN: | 2159-6867 |
| Titel des übergeordneten Werks (Englisch): | MRS communications / a publication of the Materials Research Society |
| Verlag: | Springer |
| Verlagsort: | Berlin |
| Publikationstyp: | Wissenschaftlicher Artikel |
| Sprache: | Englisch |
| Datum der Erstveröffentlichung: | 01.08.2021 |
| Erscheinungsjahr: | 2021 |
| Datum der Freischaltung: | 01.03.2024 |
| Freies Schlagwort / Tag: | (NMR); Biomaterials; Biomimetic; Mass spectrometry; Nuclear magnetic resonance |
| Band: | 11 |
| Ausgabe: | 4 |
| Seitenanzahl: | 9 |
| Erste Seite: | 402 |
| Letzte Seite: | 410 |
| Fördernde Institution: | Helmholtz AssociationHelmholtz Association; Helmholtz Association through Helmholtz Graduate School of Macromolecular Bioscience (MacroBio) [VH-GS-503] |
| Organisationseinheiten: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| DDC-Klassifikation: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Peer Review: | Referiert |
| Publikationsweg: | Open Access / Hybrid Open-Access |
| Lizenz (Deutsch): |  CC-BY - Namensnennung 4.0 International |
