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Contemplating 1,2,4-Thiadiazole-Inspired Cyclic Peptide Mimics: A Computational Investigation.
- Source :
-
Australian Journal of Chemistry . 2019, Vol. 72 Issue 11, p894-899. 6p. - Publication Year :
- 2019
-
Abstract
- Marine derived cyclic peptides have inspired chemists for decades as the cavitand architecture can be compared with macrocyclic ligands, and hence easily conceived as mediators of metal-ion transport. Lissoclinamide 5 and ascidiacyclamide are two such cyclic peptides that have received much attention both for their metal ion complexation properties and biological activity; the metal ion binding properties of mimics of these two systems have been reported. Reported herein is a computational study aimed at evaluating the stability, and potential for copper(ii) ion binding by lissoclinamide 5 mimics that substitute the naturally occurring 4-carboxy-1,3-thiazole units for novel valine- and phenylalanine-derived 1,2,4-thiadiazole units. Our results suggest that one lissoclinamide 5 mimic, 1,2,4-thiadiazole (TDA)-lissoclinamide 9 , may be capable of forming a complex with one CuII ion, [Cu(9 -H)(H2O)]+. A complex with two CuII ions, [Cu2(9 -H)(μ-OH)]2+, was also considered. These results set the stage for synthetic and experimental metal binding studies. 1,2,4-Thiadiazole-lissoclinamide 9 , a next generation mimic design, was evaluated in silico for metal binding aptitude towards CuII ions. DFT calculations suggest that TDA-lissoclinamide may be capable of forming a complex with one CuII ion, [Cu(9 -H)(H2O)]+. These results underpin future synthetic and experimental metal binding studies. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00049425
- Volume :
- 72
- Issue :
- 11
- Database :
- Academic Search Index
- Journal :
- Australian Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 139625972
- Full Text :
- https://doi.org/10.1071/CH19248