Investigations on the growth and characterization of l-citrulline oxalate monohydrate single crystal

Sreevalsa, V.G.; Jayalekshmi, S.

doi:10.1016/j.jcrysgro.2011.03.017

Cited by 13 publications

(6 citation statements)

References 13 publications

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“…A coupled mode corresponding to the scissoring mode(CH2) of the hydrocarbon chain coupled with the stretching mode of the carboxylic group (O=C-O − ) and ring stretching (C=C, C=N) could be assigned to the intense band at 1318 cm −1 . The nitrate ion could be recognized with a strong peak at 1036 cm −1 [47][48][49]. A vibrational analysis based on a comparison of the calculated and experimental normal vibration modes was carried out to confirm the binding mode of the complex.…”

Section: Raman Spectroscopymentioning

confidence: 99%

D,L-Citrullinato-bipyridine Copper Complex: Experimental and Theoretical Characterization

Ramírez-Contreras,

García-García,

Mendoza

et al. 2023

Crystals

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Citrulline is a non-protein amino acid that acts as a metabolic intermediate in the urea cycle and arginine synthesis. It is present in some foods, although its name derives from watermelon (Citrullus vulgaris), from which it was first identified. Under normal conditions, Citrulline exists as a zwitterion in aqueous solutions since its carboxylic and amine groups can act as Lewis donors to chelate metal cations. In addition, Citrulline possesses in the aliphatic chain a terminal ureide group, which could also coordinate. Although Citrulline is comparable to other classical amino acids, its coordination chemistry has yet to be explored. Only two metal complexes have been reported, and the copper complex is a polymeric and insoluble material. As part of our search for active Casiopeina® analogs, we created a more soluble complex by combining 2,2′-Bipyridine into a new mixed material, resulting in the mononuclear complex [Cu(Bipy)(Citr)(H2O)(NO3)]·H2O. Single-crystal X-ray diffraction, spectroscopic methods (FT-IR, UV-Vis, Raman), and mass spectrometry characterized the material. Interestingly, both isomers of Citrulline, R(D), and S(L) are present in the same crystal. In addition, the molecular structure and electronic properties of the complex were calculated using density functional theory (DFT). Non-covalent interactions were characterized using the atoms-in-molecules (AIM) approach and Hirshfeld surface (HS) analysis. This ternary complex containing Citrulline and 2,2′-Bipyridine will be used for docking calculations and preliminary biological studies using calf thymus DNA (CT-DNA) and plasmid pUC19 as a first approximation to cytotoxic activity against cancer cell lines.

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Section: Raman Spectroscopymentioning

confidence: 99%

D,L-Citrullinato-bipyridine Copper Complex: Experimental and Theoretical Characterization

Ramírez-Contreras,

García-García,

Mendoza

et al. 2023

Crystals

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“…In the review by Curis et al, several crystal structures of l -citrulline, a zwitterion, have been listed comprising one anhydrous crystal structure, one dihydrate, , and three salts with l -citrulline: a hydrochloride, , a perchlorate, and a co-crystal with l -malic acid . Another salt, l -citrulline oxalate monohydrate, has been published recently . Despite l -citrulline being a flexible molecule with six torsion angles, Curis et al recognized only two main conformations of l -citrulline in the various crystalline forms, which they confirmed by molecular dynamics simulations …”

Section: Introductionmentioning

confidence: 97%

“…8 Another salt, L-citrulline oxalate monohydrate, has been published recently. 9 Despite L-citrulline being a flexible molecule with six torsion angles, Curis et al recognized only two main conformations of L-citrulline in the various crystalline forms, which they confirmed by molecular dynamics simulations. 1 The flexibility of L-citrulline suggests a capacity to crystallize in different crystalline forms or polymorphs.…”

Section: ■ Introductionmentioning

confidence: 99%

On the Polymorphism of l-Citrulline: Crystal Structure and Characterization of the Orthorhombic δ Form

Allouchi

Nicolaı̈

Céolin

et al. 2014

Crystal Growth & Design

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Solid-state properties of active pharmaceutical compounds are closely related to their dissolution behavior and bioavailability, and understanding their phase behavior leads to better control in the drug formulation process. l-Citrulline is an amino acid, which is known to exhibit polymorphism; however, only the structure of the α form is reported in the literature. The structure of the δ form has been elusive due to lack of good quality single crystals. It has been found to be orthorhombic P212121 with the cell parameters a, b, and c respectively 14.895(5) Å, 9.852(2) Å, and 5.353(2) Å. The unit cell contains four molecules, and its volume is 785.5(4) Å3. Both the α form and the δ form possess uniaxial negative thermal expansion along the direction of the charge exchange of the l-citrulline zwitterions. In mixtures containing solid and saturated aqueous solution, the α form quickly transforms in a dihydrate, whereas the δ phase persists for over three weeks. Although the evidence is not conclusive, the δ phase is most likely the more stable form and most suitable for storage.

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“…The peaks at 1463, 1460, 1327, and 1297 cm −1 coincide with those reported for L-Citrulline for CH 2 scissor, and at 1127, 990 cm −1 for CH twist. The band at 1453 cm −1 is associated with the CH 2 bend, 1312 cm −1 is associated with the wiggle of CH 2 , 1279 cm −1 can be identified with the twisting of CH 2 , 682 cm −1 belongs to the COO bend, 567 cm −1 associates with the C-O bond rocking in the carboxyl plane and 289 cm −1 is associated with a rocking C-C bond [65][66][67][68][69][70].…”

Section: Raman Spectroscopymentioning

confidence: 99%

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

Ramírez-Contreras

García-García²,

Sánchez-Gaytán³

et al. 2022

Crystals

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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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Investigations on the growth and characterization of l-citrulline oxalate monohydrate single crystal

Cited by 13 publications

References 13 publications

D,L-Citrullinato-bipyridine Copper Complex: Experimental and Theoretical Characterization

D,L-Citrullinato-bipyridine Copper Complex: Experimental and Theoretical Characterization

On the Polymorphism of l-Citrulline: Crystal Structure and Characterization of the Orthorhombic δ Form

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

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