The crystal structure of CaCl<sub>2</sub>.glycylglycylglycine.3H<sub>2</sub>O

Helm, D. van der; Willoughby, T. V.

doi:10.1107/s0567740869005632

Cited by 42 publications

(13 citation statements)

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“…Observed shifting of all proton signals is also consistent with tetradentate ligand coordination as any shift, either upfield or downfield, this is not solely indicative of all Lewis bases participating in magnesium chelation as coordination of magnesium to acids has been shown to exhibit an effect on not only the α proton, but on β and γ protons as well; with diminishing impact the farther the proton is from the coordination site [47][48][49]. This conclusion coincides with findings first reported by Martell et al [57] and later supported by Van der Helm et al [58] Martell showed, via titration experiments, that HG 3 acted as a tetradentate ligand with copper and cobalt [57]. Martell's findings also supported two bound water molecules when in aqueous solution [57].…”

Section: Synthesis Of Magnesium Triglycine ([Mg(g3)(h2o)2]oh-(mgg3)supporting

confidence: 87%

Synthesis and Chemical and Biological Evaluation of a Glycine Tripeptide Chelate of Magnesium

Case

Zubieta

Gonzalez³

et al. 2021

Molecules

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Magnesium (Mg2+) plays a crucial role in over 80% of all metabolic functions. It is becoming increasingly apparent that magnesium deficiency (hypomagnesemia) may play an important role in chronic disease. To counteract magnesium deficiency, there is an unmet clinical need to develop new fully characterized, highly bioavailable, and substantially water-soluble magnesium supplements. To this end, triglycine (HG3), a tripeptide of the amino acid glycine, was chosen as a chelating ligand for magnesium, given its natural occurrence and water solubility, and entropically-driven metal binding. Herein, we discuss the synthesis, chemical and physical characterization, and cellular uptake of a magnesium triglycine chelate (MgG3), an octahedral complex with extraordinary water solubility and improved cellular uptake in CaCo-2 cells than select commonly used magnesium supplements.

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Section: Synthesis Of Magnesium Triglycine ([Mg(g3)(h2o)2]oh-(mgg3)supporting

confidence: 87%

Synthesis and Chemical and Biological Evaluation of a Glycine Tripeptide Chelate of Magnesium

Case

Zubieta

Gonzalez³

et al. 2021

Molecules

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“…There is neither direct contact between the Ca ion and the C1 ion, nor contact between the Ca ion and the amino nitrogen atom of the sarcosine molecule. This is just the same as found in CaCl2.glycylglycylglycine.3H20 (Van der Helm & Willoughby, 1969). The arrangement of the neighbouring molecules around the Ca ion is shown in Figs. 3 and 7.…”

Section: Structure Determinationsupporting

confidence: 59%

The crystal structure of trissarcosine calcium chloride

Ashida¹,

Bando²,

Kakudo³

1972

Acta Crystallogr Sect B

106

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“…The protonation of the peptide led to a shift of corresponding amide vibrations The new band at 1749 cm À1 corresponds to the C¼O of the -COOH fragment. The data for the higher Gly-analogs revealed that the values for NH are typical of trans-amide fragments where the frequency of the IR band corresponding to NH is observed within the range of 1560-1530 cm À1 (table 1) [116][117][118][119][120][121][122][123][124][125][126][127][128][129][130][131][132][133][134][135]. However, the strong overlapping of the spectroscopic patterns requires the application of other physical methods, such as NMR and MS.…”

Section: Introductionmentioning

confidence: 98%

Protonation and coordination ability of small peptides – theoretical and experimental approaches for elucidation

Lamshöft

Ivanova

2011

Journal of Coordination Chemistry

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This review deals with modern theoretical and experimental approaches as well as structural elucidation of small peptides (SP), their protonated forms and metal complexes. Free peptide bond rotation in amino acids (AA) and peptides yielded various conformers, which may possess differing biological activities. Inter-and/or intramolecular stacking observed in aromatic SP is another phenomenon typical for both peptide salts and complexes. These phenomenological effects can be successfully studied, both theoretically and experimentally, using a combination of the theoretical approximations and physical methods, such as electronic absorption spectroscopy, vibrational spectroscopy (including IR and Raman), nuclear magnetic resonance, mass spectrometry, as well as single-crystal X-ray diffraction. The physical and chemical properties of these systems can be precisely calculated by ab initio and DFT methods, varying basis sets and the results obtained allow elucidation of their conformations as a function of the reaction conditions (pH, type of the solvent, temperature, metal to ligand molar ratio). Although the 3-D structures of many peptides have been determined over the past decades, peptide crystallization is still a major obstacle to crystallographic work and the presence of chiral center/s adds further difficulties. For this reason, a specific part of the review is focused on the study of the absolute structure of the peptides, their salts and metal complexes, discussing the conformational preferences of the peptides during these processes. The available crystallographic data for metal complexes are successfully used for the correlation between the structures and the spectroscopic properties.

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The crystal structure of CaCl₂.glycylglycylglycine.3H₂O

Cited by 42 publications

References 0 publications

Synthesis and Chemical and Biological Evaluation of a Glycine Tripeptide Chelate of Magnesium

Synthesis and Chemical and Biological Evaluation of a Glycine Tripeptide Chelate of Magnesium

The crystal structure of trissarcosine calcium chloride

Protonation and coordination ability of small peptides – theoretical and experimental approaches for elucidation

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The crystal structure of CaCl2.glycylglycylglycine.3H2O

Cited by 42 publications

References 0 publications

Synthesis and Chemical and Biological Evaluation of a Glycine Tripeptide Chelate of Magnesium

Synthesis and Chemical and Biological Evaluation of a Glycine Tripeptide Chelate of Magnesium

The crystal structure of trissarcosine calcium chloride

Protonation and coordination ability of small peptides – theoretical and experimental approaches for elucidation

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Product

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The crystal structure of CaCl₂.glycylglycylglycine.3H₂O