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EnglishA family of four self-assembling lipopeptides containing Ala-Lys peptides attached to a C16 aliphatic chain were synthesised. These compounds form two enantiomeric pairs that bear a diastereomeric relationship to one another (C16 -l-Ala-l-Lys/C16 -d-Ala-d-Lys) and (C16 -d-Ala-l-Lys/C16 -l-Ala-d-Lys). These diastereomeric pairs have very different critical micelle concentrations (CMCs). The self-assembled multivalent (SAMul) systems bind biological polyanions as a result of the cationic lysine groups on their surfaces. For heparin binding, there was no significant enantioselectivity, but there was a binding preference for the diastereomeric assemblies with lower CMCs. Conversely, for DNA binding, there was significant enantioselectivity for systems displaying d-lysine ligands, with a further slight preference for attachment to l-alanine, with the CMC being irrelevant.
| Titolo: | Enantiomeric and Diastereomeric Self-Assembled Multivalent Nanostructures: Understanding the Effects of Chirality on Binding to Polyanionic Heparin and DNA |
| Autori: | |
| Data di pubblicazione: | 2018 |
| Data ahead of print: | 15-mag-2018 |
| Stato di pubblicazione: | Epub ahead of print |
| Rivista: | |
| Abstract: | A family of four self-assembling lipopeptides containing Ala-Lys peptides attached to a C16 aliphatic chain were synthesised. These compounds form two enantiomeric pairs that bear a diastereomeric relationship to one another (C16 -l-Ala-l-Lys/C16 -d-Ala-d-Lys) and (C16 -d-Ala-l-Lys/C16 -l-Ala-d-Lys). These diastereomeric pairs have very different critical micelle concentrations (CMCs). The self-assembled multivalent (SAMul) systems bind biological polyanions as a result of the cationic lysine groups on their surfaces. For heparin binding, there was no significant enantioselectivity, but there was a binding preference for the diastereomeric assemblies with lower CMCs. Conversely, for DNA binding, there was significant enantioselectivity for systems displaying d-lysine ligands, with a further slight preference for attachment to l-alanine, with the CMC being irrelevant. |
| Handle: | http://hdl.handle.net/11368/2926779 |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1002/anie.201803298 |
| URL: | https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201803298 |
| Appare nelle tipologie: | 1.1 Articolo in Rivista |
File in questo prodotto:
| File | Descrizione | Tipologia | Licenza | |
|---|---|---|---|---|
| Kiri Manuscript FINAL.pdf | Main paper | Bozza finale post-referaggio (post-print) | Digital Rights Management non definito | Open Access Visualizza/Apri |
| Thornalley_et_al-2018-Angewandte_Chemie_International_Edition.pdf | Documento in Versione Editoriale | Copyright Editore | Administrator Richiedi una copia |
