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Article

Bis-Citrullinato Copper(II) Complex: Synthesis, Crystal Structure, and Non-Covalent Interactions

by
Diego Ramírez-Contreras
1,
Amalia García-García
1,2,
Brenda L. Sánchez-Gaytán
1,
Laura E. Serrano-de la Rosa
3,
Francisco J. Melendez
4,
Duane Choquesillo-Lazarte
5,
Antonio Rodríguez-Diéguez
2,
María Eugenia Castro
1,* and
Enrique González-Vergara
1,*
1
Centro de Química del Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, 18 sur y Av. San Claudio, Col. San Manuel, Puebla 72570, Mexico
2
Departamento de Química Inorgánica, Facultad de Ciencias, Universidad de Granada, Av. Fuentenueva S/N, 18071 Granada, Spain
3
Laboratorio Central del Instituto de Física “Luis Rivera Terrazas” (IFUAP), Benemérita Universidad Autónoma de Puebla, 18 sur y Av. San Claudio, Col. San Manuel, Puebla 72570, Mexico
4
Lab. de Química Teórica, Centro de Investigación, Depto. de Fisicoquímica, Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, 22 sur y Av. San Claudio, Col. San Manuel, Puebla 72570, Mexico
5
Laboratorio de Estudios Cristalográficos, IACT, CSIC-UGR, Av. Las Palmeras nº4, 18100 Granada, Spain
*
Authors to whom correspondence should be addressed.
Crystals 2022, 12(10), 1386; https://doi.org/10.3390/cryst12101386
Submission received: 6 September 2022 / Revised: 22 September 2022 / Accepted: 26 September 2022 / Published: 29 September 2022
(This article belongs to the Special Issue Synthesis, Crystal Structures and Hirshfeld Surface Analysis of Coordination Compounds (Volume II))
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Abstract

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.
Keywords: Citrulline; copper; DFT calculations; Hirshfeld surface analysis; non-covalent interactions Citrulline; copper; DFT calculations; Hirshfeld surface analysis; non-covalent interactions

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MDPI and ACS Style

Ramírez-Contreras, D.; García-García, A.; Sánchez-Gaytán, B.L.; Serrano-de la Rosa, L.E.; Melendez, F.J.; Choquesillo-Lazarte, D.; Rodríguez-Diéguez, A.; Castro, M.E.; González-Vergara, E. Bis-Citrullinato Copper(II) Complex: Synthesis, Crystal Structure, and Non-Covalent Interactions. Crystals 2022, 12, 1386. https://doi.org/10.3390/cryst12101386

AMA Style

Ramírez-Contreras D, García-García A, Sánchez-Gaytán BL, Serrano-de la Rosa LE, Melendez FJ, Choquesillo-Lazarte D, Rodríguez-Diéguez A, Castro ME, González-Vergara E. Bis-Citrullinato Copper(II) Complex: Synthesis, Crystal Structure, and Non-Covalent Interactions. Crystals. 2022; 12(10):1386. https://doi.org/10.3390/cryst12101386

Chicago/Turabian Style

Ramírez-Contreras, Diego, Amalia García-García, Brenda L. Sánchez-Gaytán, Laura E. Serrano-de la Rosa, Francisco J. Melendez, Duane Choquesillo-Lazarte, Antonio Rodríguez-Diéguez, María Eugenia Castro, and Enrique González-Vergara. 2022. "Bis-Citrullinato Copper(II) Complex: Synthesis, Crystal Structure, and Non-Covalent Interactions" Crystals 12, no. 10: 1386. https://doi.org/10.3390/cryst12101386

APA Style

Ramírez-Contreras, D., García-García, A., Sánchez-Gaytán, B. L., Serrano-de la Rosa, L. E., Melendez, F. J., Choquesillo-Lazarte, D., Rodríguez-Diéguez, A., Castro, M. E., & González-Vergara, E. (2022). Bis-Citrullinato Copper(II) Complex: Synthesis, Crystal Structure, and Non-Covalent Interactions. Crystals, 12(10), 1386. https://doi.org/10.3390/cryst12101386

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