Bis-Citrullinato Copper(II) Complex: Synthesis, Crystal Structure, and Non-Covalent Interactions
Citrulline (C6H13N3O3) is a non-protein amino acid found in watermelon. In physiological conditions, it is almost entirely present as a zwitterion, so its carboxylic and amine groups can act as Lewis donors, chelating metallic cations. In addition, Citrulline possesses a terminal ureide group of the...
| Autores: | , , , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2022 |
| País: | España |
| Institución: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/282213 |
| Acceso en línea: | http://hdl.handle.net/10261/282213 |
| Access Level: | acceso abierto |
| Palabra clave: | Citrulline Copper DFT calculations Hirshfeld surface analysis Non-covalent interactions |
| Sumario: | Citrulline (C6H13N3O3) is a non-protein amino acid found in watermelon. In physiological conditions, it is almost entirely present as a zwitterion, so its carboxylic and amine groups can act as Lewis donors, chelating metallic cations. In addition, Citrulline possesses a terminal ureide group of the aliphatic chain, which appears to be non-innocent. Although Citrulline is similar to other classical amino acids, only one coordination complex has been reported in the Cambridge Crystallographic Database. As part of our search for Casiopeina® analogs, we synthesized and characterized the copper bis-citrullinato complex, [Cu(Citr)2]n. The compound was described using UV-Vis, Infrared, and Raman spectroscopy, together with single-crystal X-ray diffraction. Computational tools were also used. The optimized structure, MEP map, IR and Raman spectra, and 1H and 13C chemical shifts were obtained with functional mPW1PW91 using 6-31G(d) basis set for N, O, C, and H atoms, and LANL2DZ basis set and ECP=LANL2DZ for the Cu atom. TD-mPW1PW91 calculations generated the UV-Vis spectrum. Finally, AIM and Hirshfeld surface analysis were used to examine non-covalent interactions. Previous investigations suggest Casiopeina®-like complexes can interact with DNA/RNA, creating potential anticancer chemicals. The [Cu(Citr)2]n complex’s polymeric nature and insolubility make it difficult for such purposes. However, the facile synthesis of D-Citrulline could be a novel way to find new applications for this interesting amino acid. |
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