2019
DOI: 10.1039/c9ra03418h
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pH-induced conformational changes in histamine in the solid state

Abstract: Histamine is one of the most basic biogenic amino-compounds, which is composed of imidazole and a flexible ethylamine side chain moiety. Histamine is known to take the form of various types of cations, free base, monocation and dication form, where its conformational change is highly sensitively to the pH conditions. The details of these changes are still controversial due to a lack of detailed information on its crystal structures.Thus, in this study, the molecular packing structures of histidine at various p… Show more

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Cited by 7 publications
(13 citation statements)
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“…Partial N6 attaches protons and simultaneously partial N8 loses protons (N τ -gauche species; Figure 1 D). Then the histamine molecule changes conformation by forming intramolecular hydrogen bonds instead of interaction with solution molecules ( Kodchakorn et al., 2019 ; Ramírez et al., 2003 ). This is the case in solutions.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Partial N6 attaches protons and simultaneously partial N8 loses protons (N τ -gauche species; Figure 1 D). Then the histamine molecule changes conformation by forming intramolecular hydrogen bonds instead of interaction with solution molecules ( Kodchakorn et al., 2019 ; Ramírez et al., 2003 ). This is the case in solutions.…”
Section: Resultsmentioning
confidence: 99%
“…In the dication form, the three nitrogen atoms all accept protons. The pH value can effectively affect the side-chain internal torsion so as to form stable ionic forms (different torsional isomers) that determine biological activities ( Kodchakorn et al., 2019 ; Mukherjee and Yadav, 2016 ; Vianello and Mavri, 2012 ). Figure 2 A depicts the low-frequency Raman spectra of the aqueous histamine solutions with three typical pH values of 11, 7.4, and 4.…”
Section: Resultsmentioning
confidence: 99%
“…The IR spectrum of HA in plot 'b' shows peaks at 1105, 3120, 2854 and 3350, 3426 cm À1 assigned to stretches of the aromatic ring, and C-H and N-H bonds of primary amines. 37 The doublet peaks of N-H stretch observed at 3350 and 3426 cm À1 due to primary amines are important to be noted. Plot 'c' represents the IR spectrum of the interacted probe with histamine and the doublet becomes a single peak here, at 3343 cm À1 evidencing the conversion of amine to amide.…”
Section: Conjugation Of Biogenic Ha Molecule With Apqdsmentioning
confidence: 97%
“…Hydrogen bonding (H-bonding) is a fundamental interaction that plays a crucial role in the stability and function of biological molecules. In particular, it is widely recognized for promoting the formation of secondary and tertiary structures of biological macromolecules, such as DNA and amino acids. , Intramolecular H-bonding can promote folded conformations and affect the electronic structure of molecules and chemical reactivity. , For example, histamine ( hist ), a biogenic amine with a structure derived from the amino acid histidine, is believed to form intramolecular H-bonds under physiological conditions. …”
mentioning
confidence: 99%
“…Techniques such as surface enhanced raman spectroscopy (SERS), , infrared (IR) spectroscopy, , nuclear magnetic resonance (NMR) spectroscopy, , X-ray diffraction analysis (XRD), and density function theory (DFT) calculations , have been used to differentiate the various conformations of hist in solid-state, solution, and gas-phase circumstances. But in solution at room temperature, H-bonding is transient so that multiple conformations coexist and can be challenging to differentiate using ensemble measurements. , …”
mentioning
confidence: 99%