First principles study on proton transfer between amino acid side chains of histidine and aspartic acid in β-structure

Sargolzaei, Mohsen; Afshar, Mohammad; Sadeghi, Mahdi; Hamidian, H.

doi:10.1134/s0022476614080332

Cited by 3 publications

(3 citation statements)

References 18 publications

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“…The binding affinity of histidine to Zn 2+ and Ca 2+ was greatly higher than Na + and K + , and could also bind to host proteins by coordinate bonds [ 14 ]. In addition, the imidazole group of histidine (His) can combine with the carboxyl group in glutamic (Glu) and aspartic (Asp), affecting the structural characteristics of peptides [ 15 ]. In comparison, the carboxyl oxygen and amino nitrogen atoms of Glu and Asp are often regarded as the calcium-binding sites in polypeptides.…”

Section: Introductionmentioning

confidence: 99%

Calcium Binding Mechanism of Soybean Peptide with Histidine Alteration by Molecular Docking Analysis and Spectroscopic Methods

Gan

Kong

Xiao

et al. 2022

Foods

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Histidine (His) carries a unique heteroaromatic imidazole side chain and plays an irreplaceable role in peptides and proteins. With the current study, we aimed to determine the characteristics and functional activities of the bone density of soy peptide–calcium complexes in which a His residue was replaced by Leu (CBP-H). Soybean peptide (CBP-H) was chemically synthesized, the binding mechanism between CBP-H and calcium ions in combination was determined with bioinformatics and spectroscopy analysis, and the difference between CBP and CBP-H was investigated. Finally, we analyzed the effect of CBP and CBP-H on osteoblasts in vitro. The results showed that CBP-H could bind to calcium ions, and the calcium coordinated with the carboxyl groups of Asp and Glu in the peptide. The nitrogen atoms of the amino group and the oxygen atoms of the carboxyl group in CBP-H significantly contributed to the coordination with Ca2+. Furthermore, the binding capacity was 36.48 ± 0.09 mg/g, similar to CBP. However, both CBP and CBP-H could promote osteogenic activity, the activity of CBP-H was 127.147%, lower than CBP (121.777%). While it had the same ability to promote intracellular calcium concentration, CBP-H could upregulate 150.12% calcium ions into the intracellular, and the rate of the rise of CBP was 158.91%, further highlighting the potential of His residues for binding calcium and treating osteoporosis.

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Section: Introductionmentioning

confidence: 99%

Calcium Binding Mechanism of Soybean Peptide with Histidine Alteration by Molecular Docking Analysis and Spectroscopic Methods

Gan

Kong

Xiao

et al. 2022

Foods

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“…1 A number of amino acids such as aspartic acid, histidine, lysine, serine, tyrosine are also typically involved. [3][4][5][6] The unique properties of arginine within natural amino acids largely rely on the basicity of its guanidinium side group, with a pK a value as high as 13.8, according to a recent revision. 7 In this way, arginine can adopt different charge states 8,9 and it is capable of promoting a broad range of biochemical processes, including essential steps of metabolic pathways, transmembrane transport or transduction.…”

Section: Introductionmentioning

confidence: 99%

Isolated complexes of the amino acid arginine with polyether and polyamine macrocycles, the role of proton transfer

Avilés–Moreno

Berden

Martínez–Haya

2017

Phys. Chem. Chem. Phys.

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The distinct basicity of the guanidinium side-group of arginine (Arg) sustains specific interactions involved in essential biochemical processes. The sensing of arginine is therefore key in modern biotechnology and bioanalysis. In this context, the development of molecular receptors based on crown ether building blocks has demonstrated great potential. We investigate the complexes formed by arginine with two benchmark macrocycles, 12-crown-4 (1,4,7,10-tetraoxacyclododecane) and its N-substituted analog cyclen (1,4,7,10-tetraazacyclododecane). Isolated complexes with a net charge +1 are characterized with infrared action vibrational spectroscopy and quantum mechanical computations in order to determine the most stable coordination arrangements and to elucidate the location of the protons involved. Remarkably, although arginine retains a net positive charge in its complex with 12-crown-4, it becomes zwitterionic in the cyclen complex. In this latter case, the guanidinium group remains protonated while a proton transfer from the carboxylic group occurs, leading to a charged -NH moiety in cyclen. Natural bond orbital analysis is employed to characterize the intermolecular H-bonds responsible for the stability of both complexes. Protonated arginine interacts with 12-crown-4 through the guanidinium side group, in a conformation that resembles the one expected for crown-Arg binding in peptidic chains. In contrast, the cyclen complex involves the coordination of the carboxylate anionic group with a N-H bond of the protonated amine group cyclen, and plausible but less relevant interactions with the guanidinium group.

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“…The proton transfer, for example, is fundamental to the chemiosmosis and, consequently, for maintaining vital activities . Hence, most of the research about acidity and basicity is now focused on molecules of biological interest, particularly, amino acids and peptides . For instance, special attention has been devoted to the identification of localization sites of atomic charge concentration during protonation of amino acids residues …”

Section: Introductionmentioning

confidence: 99%

A quantum theory atoms in molecules investigation of Lewis base protonation

Silva

Terrabuio

Haiduke

2016

Int. J. Quantum Chem.

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This investigation uses atomic properties derived from the quantum theory of atoms in molecules formalism to rationalize the infrared intensity of the stretching vibration that arises as a Lewis base (B) is protonated (B‐H mode). Moreover, the interacting quantum atom (IQA) partition is employed to evaluate the energetics of protonation. All calculations are performed at the CCSD/cc‐pVQZ level except by the IQA analysis, which is carried out by means of the B3LYP/cc‐pVQZ//CCSD/cc‐pVQZ treatment. First, an efficiency scale is established for Lewis bases in terms of the electronic charge transfer potential. Next, this study shows that the intensity of the B‐H stretching depends mostly on the electronic charge amount transferred to the proton. Thus, intensity data provide empirical assessment of Lewis base charge transfer efficiency. Finally, the group separation observed during correlation of proton affinities and electronic charge transfer potential is explained by the interaction energy between fragments of the protonated system.

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First principles study on proton transfer between amino acid side chains of histidine and aspartic acid in β-structure

Cited by 3 publications

References 18 publications

Calcium Binding Mechanism of Soybean Peptide with Histidine Alteration by Molecular Docking Analysis and Spectroscopic Methods

Calcium Binding Mechanism of Soybean Peptide with Histidine Alteration by Molecular Docking Analysis and Spectroscopic Methods

Isolated complexes of the amino acid arginine with polyether and polyamine macrocycles, the role of proton transfer

A quantum theory atoms in molecules investigation of Lewis base protonation

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