Directed coordination study of [Pd(en)(H2O)2]2+ with hetero-tripeptides containing C-terminus methyl esters employing NMR spectroscopy

Monger, Lindsey J.; Rúnarsdóttir, Gerður Rún; Suman, Sigridur G.

doi:10.1007/s00775-020-01804-0

Cited by 3 publications

(8 citation statements)

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“…The coordination of tripeptide- 1 with Pd(II) and degree of hydrolysis are highly dependent on pH, rendering standard synthetic techniques ineffective [ 31 ]. Methods to establish an aqueous synthetic strategy to form neutral tetradentate Pd(II) complexes were explored [ 36 ].…”

Section: Resultsmentioning

confidence: 99%

“…When coordinated to a metal center via the N-terminal amine and the nearest amide, the peptide forms a 6-membered chelate. In an aqueous medium at neutral pH this system presented a competing coordination to the side chain carbonyl forming the bidentate 5-membered κ 2 [NH 2 ,O] chelate instead of the κ 3 [NH 2 ,N,N] amide backbone [ 31 ]. The κ 4 [NH 2 ,N,N,O] chelated complex could be formed in basic aqueous conditions at a pH value of ~9.…”

Section: Resultsmentioning

confidence: 99%

“…Aqueous coordination studies of 3 with Pd(en)(H 2 O) 2+ revealed that the tryptophan indole participated in coordination [ 31 ]. The 1 H-NMR study revealed that at a low pH the NH 2 coordinated as expected and chelation continued to the Ala amide.…”

Section: Resultsmentioning

confidence: 99%

“…In order to avoid this undesirable reaction, non-aqueous conditions were employed. In previous work we described the synthesis of three new tripeptide ligands and investigated the effects of pH on their coordination to [Pd(en)(H 2 O)] 2+ [ 31 ]. The ligands were designed to form either κ 4 [5,5,5] ( Figure 1 b) or κ 4 [6,5,5] ( Figure 1 c) membered ring tetradentate ligands, allowing for an adjustable ligand design for ligands 1 and 2 ( Figure 2 ).…”

Section: Introductionmentioning

confidence: 99%

“…In addition to the primary amine and carboxylate C-terminal functional groups, indole complexation was reported through the secondary amine [ 32 ], the indole C2, [ 33 , 34 ], and the C3 carbon [ 35 ]. The tripeptides exhibited their maximum expected chelating ring sizes at the N-terminus and aqueous in situ studies confirmed it is possible to form complexes with κ 4 [ n ,5,5] ( n = 8, 6, 5) chelates [ 31 ]. The molecular ions of the complexes were found and matched with their simulated isotope patterns in the ESI MS of the complexes.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization, and Reaction Studies of Pd(II) Tripeptide Complexes

et al. 2021

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The aqueous synthesis of Pd(II) complexes with alkylated tripeptides led to the hydrolysis of the peptides at low pH values and mixtures of complexed peptides were formed. A non-aqueous synthetic route allowed the formation and isolation of single products and their characterization. Pd(II) complexes with α-Asp(OR)AlaGly(OR), β-Asp(OR)AlaGly(OR), and TrpAlaGly(OR) (R = H or alkyl) as tri and tetradentate chelates were characterized. The tridentate coordination mode was accompanied by a fourth monodentate ligand that was shown to participate in both ligand exchange reactions and a direct removal to form the tetradentate coordination mode. The tetradentate coordination revealed a rare a hemi labile carbonyl goup coordination mode to Pd(II). Reactivity with small molecules such as ethylene, acids, formate, and episulfide was investigated. Under acidic conditions and in the presence of ethylene; acetaldehyde was formed. The Pd(II) is a soft Lewis acid and thiophilic and the complexes abstract sulfur from episulfide at apparent modest catalytic rates. The complexes adopt a square planar geometry according to a spectroscopic analysis and DFT calculations that were employed to evaluate the most energetically favorable coordination geometry and compared with the observed infrared and NMR data.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization, and Reaction Studies of Pd(II) Tripeptide Complexes

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Synthesis and Biological Activities of Some Metal Complexes of Peptides: A Review

Marinova,

Tamahkyarova

2024

BioTech

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Peptides, both natural and synthetic, are well suited for a wide range of purposes and offer versatile applications in different fields such as biocatalysts, injectable hydrogels, tumor treatment, and drug delivery. The research of the better part of the cited papers was conducted using various database platforms such as MetalPDB. The rising prominence of therapeutic peptides encompasses anticancer, antiviral, antimicrobial, and anti-neurodegenerative properties. The metals Na, K, Mg, Ca, Fe, Mn, Co, Cu, Zn, and Mo are ten of the twenty elements that are considered essential for life. Crucial for understanding the biological role of metals is the exploration of metal-bound proteins and peptides. Aside from essential metals, there are other non-essential metals that also interact biologically, exhibiting either therapeutic or toxic effects. Irregularities in metal binding contribute to diseases like Alzheimer’s, neurodegenerative disorders, Wilson’s, and Menkes disease. Certain metal complexes have potential applications as radiopharmaceuticals. The examination of these complexes was achieved by preforming UV–Vis, IR, EPR, NMR spectroscopy, and X-ray analysis. This summary, although unable to cover all of the studies in the field, offers a review of the ongoing experimentation and is a basis for new ideas, as well as strategies to explore and gain knowledge from the extensive realm of peptide-chelated metals and biotechnologies.

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Studying Peptide-Metal Ion Complex Structures by Solution-State NMR

Shalev

2022

IJMS

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Metal chelation can provide structural stability and form reactive centers in metalloproteins. Approximately one third of known protein structures are metalloproteins, and metal binding, or the lack thereof, is often implicated in disease, making it necessary to be able to study these systems in detail. Peptide-metal complexes are both present in nature and can provide a means to focus on the binding region of a protein and control experimental variables to a high degree. Structural studies of peptide complexes with metal ions by nuclear magnetic resonance (NMR) were surveyed for all the essential metal complexes and many non-essential metal complexes. The various methods used to study each metal ion are presented together with examples of recent research. Many of these metal systems have been individually reviewed and this current overview of NMR studies of metallopeptide complexes aims to provide a basis for inspiration from structural studies and methodology applied in the field.

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Directed coordination study of [Pd(en)(H2O)2]2+ with hetero-tripeptides containing C-terminus methyl esters employing NMR spectroscopy

Cited by 3 publications

References 72 publications

Synthesis, Characterization, and Reaction Studies of Pd(II) Tripeptide Complexes

Synthesis, Characterization, and Reaction Studies of Pd(II) Tripeptide Complexes

Synthesis and Biological Activities of Some Metal Complexes of Peptides: A Review

Studying Peptide-Metal Ion Complex Structures by Solution-State NMR

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