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.
| Author details: | Makafui Y. FolikumahORCiDGND, Marc BehlORCiDGND, Andreas LendleinORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1557/s43579-021-00041-z |
| ISSN: | 2159-6859 |
| ISSN: | 2159-6867 |
| Title of parent work (English): | MRS communications / a publication of the Materials Research Society |
| Publisher: | Springer |
| Place of publishing: | Berlin |
| Publication type: | Article |
| Language: | English |
| Date of first publication: | 2021/08/01 |
| Publication year: | 2021 |
| Release date: | 2024/03/01 |
| Tag: | (NMR); Biomaterials; Biomimetic; Mass spectrometry; Nuclear magnetic resonance |
| Volume: | 11 |
| Issue: | 4 |
| Number of pages: | 9 |
| First page: | 402 |
| Last Page: | 410 |
| Funding institution: | Helmholtz AssociationHelmholtz Association; Helmholtz Association through Helmholtz Graduate School of Macromolecular Bioscience (MacroBio) [VH-GS-503] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Peer review: | Referiert |
| Publishing method: | Open Access / Hybrid Open-Access |
| License (German): |  CC-BY - Namensnennung 4.0 International |
