Amino acid-type interactions of L-3,4-dihydroxyphenylalanine with transition metal ions: An experimental and theoretical investigation

Mandal, Shilpi; Das, Gunajyoti; Askari, Hassan

doi:10.1016/j.molstruc.2015.06.063

Cited by 11 publications

(3 citation statements)

References 57 publications

(67 reference statements)

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“…A bis-N,Ocoordination mode is also consistent with the assignment based on solution chemistry at pH 5.5 for the analogous chiral complex with l-DOPA (Boggess & Martin, 1975). Recently, a copper(II) l-DOPA complex was synthesized by grinding dehydrated copper acetate monohydrate with l-DOPA (Mandal et al, 2015). The complex obtained in this manner has a similar powder X-ray diffraction pattern to that of CuLD, suggestive of the same compound.…”

Section: Resultssupporting

confidence: 77%

cis-Bis(L-DOPA-κ² N,O)copper(II) monohydrate: synthesis, crystal structure, and approaches to the analysis of pseudosymmetry

et al. 2021

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The crystal structure of the cis isomer of cis-bis(L-DOPA-κ2 N,O)copper(II) monohydrate (L-DOPA is 3,4-dihydroxy-L-phenylalanine) (CuLD), [Cu(C9H10NO4)2]·H2O, is a singular example of a structurally characterized, homoleptic, crystalline metal L-DOPA complex. CuLD crystallizes in the space group P21, with Z′ = 2. The two independent molecules are square planar, and are interconnected by a linear hydrogen-bonded chain containing 12 independent hydrogen bonds. The copper ions in both molecules have weak apical intermolecular Cu...O interactions [2.739 (2) and 2.973 (2) Å] with catechol –OH groups. A survey of the Cambridge Structural Database suggested that cis and trans isomers of Cu(NH2–C–CO2)2 amino acid complexes are equally likely to occur. 12 strong O—H...O and N—H...O hydrogen bonds stabilize an unusual linear arrangement of the Cu complexes. The Cu...Cu′ distances along the chain are nearly equal [5.0739 (3) and 5.1107 (3) Å] and the Cu...Cu′...Cu angles are nearly linear [176.75 (1)°]. The MATCH procedure available in the Oxford University Crystals for Windows package was used to carry out a detailed analysis of the relationship between the two independent molecules. MATCH has some particular advantages in studying the details of pseudosymmetry, which include: (i) no atomic-order requirements; (ii) the pseudosymmetry matrix is readily available, which allows quick insight into the symmetry elements involved and their location; and (iii) the differences between molecular centroids, as well as between all atomic positions and torsion angles, are listed. A tutorial presentation is designed to attract new users to the technique. In the present case, a search for a pseudosymmetric relationship between the two independent molecules showed that they are related by a pseudo-42 axis along the crystallographic c direction. A detailed analysis shows that the pseudo-42 symmetry is disrupted by torsions about the CH2—C(ipso) bonds, and that there is no supergroup that can be used to describe the crystal structure.

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Section: Resultssupporting

confidence: 77%

cis-Bis(L-DOPA-κ² N,O)copper(II) monohydrate: synthesis, crystal structure, and approaches to the analysis of pseudosymmetry

et al. 2021

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“…The results suggest that PL-DOPA and PL-5-HTP, in their zwitterionic state, may have resistance to nonspecific protein adsorption. The zwitterionic nature of these two compounds can be attributed to the presence of both amine groups and carboxyl groups in their structures. − Because of the excellent antifouling properties and biocompatibility of these zwitterionic materials, they have been considered as a new generation of antifouling materials for many biomedical applications. ,− …”

Section: Resultsmentioning

confidence: 99%

Properties of Electropolymerized Dopamine and Its Analogues

Wang

Young

et al. 2018

Langmuir

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This work reports a study of electropolymerization kinetics, film thickness, stability, and antifouling properties of polydopamine (PDA) and its three analogues: poly(3-(3,4-dihydroxyphenyl)-l-alanine) (PL-DOPA), poly(5-hydroxytryptophan) (PL-5-HTP), and poly(Adrenalin) (PAdrenalin). It was observed that the number of the hydroxyl groups on the benzene ring and the type (primary vs secondary) of amine group significantly affect the electropolymerization kinetics and thus the thickness of the obtained polymer films. Monomers with two hydroxyl groups (except Adrenalin) resulted in films that were thicker (∼10-15 nm) than the one with only one hydroxyl group (PL-5-HTP) (∼5-8 nm) under similar conditions. Adrenalin containing a secondary amino group could not be deposited onto the ITO substrate, while the other three compounds containing a primary amino group completely covered the ITO. The PDA films had better electrochemical stability than the other films. No film showed stable antifouling surfaces against protein.

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“…In addition, prior research has focused on solvent-free syntheses [19]. Azo dyes are compounds that contain azo groups linked to methane or an aromatic sp 2 -hybridized C-atom.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of azo-linked diindolyl methanes using Fe³⁺-montmorillonite K10 under solvent-free condition

Nikpassand

Fekri

Mousavi

2017

Journal of Taibah University for Science

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Amino acid-type interactions of L-3,4-dihydroxyphenylalanine with transition metal ions: An experimental and theoretical investigation

Cited by 11 publications

References 57 publications

cis-Bis(L-DOPA-κ² N,O)copper(II) monohydrate: synthesis, crystal structure, and approaches to the analysis of pseudosymmetry

cis-Bis(L-DOPA-κ² N,O)copper(II) monohydrate: synthesis, crystal structure, and approaches to the analysis of pseudosymmetry

Properties of Electropolymerized Dopamine and Its Analogues

Synthesis of azo-linked diindolyl methanes using Fe³⁺-montmorillonite K10 under solvent-free condition

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Amino acid-type interactions of L-3,4-dihydroxyphenylalanine with transition metal ions: An experimental and theoretical investigation

Cited by 11 publications

References 57 publications

cis-Bis(L-DOPA-κ2 N,O)copper(II) monohydrate: synthesis, crystal structure, and approaches to the analysis of pseudosymmetry

cis-Bis(L-DOPA-κ2 N,O)copper(II) monohydrate: synthesis, crystal structure, and approaches to the analysis of pseudosymmetry

Properties of Electropolymerized Dopamine and Its Analogues

Synthesis of azo-linked diindolyl methanes using Fe3+-montmorillonite K10 under solvent-free condition

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Product

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cis-Bis(L-DOPA-κ² N,O)copper(II) monohydrate: synthesis, crystal structure, and approaches to the analysis of pseudosymmetry

cis-Bis(L-DOPA-κ² N,O)copper(II) monohydrate: synthesis, crystal structure, and approaches to the analysis of pseudosymmetry

Synthesis of azo-linked diindolyl methanes using Fe³⁺-montmorillonite K10 under solvent-free condition