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231225s2020 xx |||||o 00| ||eng c |
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|a 10.1002/mrc.4990
|2 doi
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|a pubmed25n1016.xml
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|a (NLM)31912552
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|a DE-627
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|e rakwb
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|a eng
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|a Kupka, Teobald
|e verfasserin
|4 aut
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|a What is the form of muscimol from fly agaric mushroom (Amanita muscaria) in water? An insight from NMR experiment supported by molecular modeling
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|c 2020
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|a Text
|b txt
|2 rdacontent
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|a ƒaComputermedien
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|2 rdamedia
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|a ƒa Online-Ressource
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|2 rdacarrier
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|a Date Completed 04.08.2021
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|a Date Revised 04.08.2021
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|a published: Print-Electronic
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|a Citation Status MEDLINE
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|a © 2020 John Wiley & Sons, Ltd.
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|a The biologically active alkaloid muscimol is present in fly agaric mushroom (Amanita muscaria), and its structure and action is related to human neurotransmitter γ -aminobutyric acid (GABA). The current study reports on determination of muscimol form present in water solution using multinuclear 1 H and 13 C nuclear magnetic resonance (NMR) experiments supported by density functional theory molecular modeling. The structures of three forms of free muscimol molecule both in the gas phase and in the presence of water solvent, modeled by polarized continuous model, and nuclear magnetic isotropic shieldings, the corresponding chemical shifts, and indirect spin-spin coupling constants were calculated. Several J-couplings observed in proton and carbon NMR spectra, not available before, are reported. The obtained experimental spectra, supported by theoretical calculations, favor the zwitterion form of muscimol in water. This structure differs from NH isomer, previously determined in dimethyl sulfoxide (DMSO) solution. In addition, positions of signals C3 and C5 are reversed in both solvents
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|a Journal Article
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|a GIAO NMR
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|a NMR in water
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|a indirect spin-spin coupling constants
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|a molecular modeling
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|a muscimol
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|a Carbon Isotopes
|2 NLM
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|a GABA-A Receptor Antagonists
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|a Protons
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|a Receptors, GABA
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|a Water
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|a 059QF0KO0R
|2 NLM
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|a Muscimol
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|a 2763-96-4
|2 NLM
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|a Carbon-13
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|a FDJ0A8596D
|2 NLM
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|a Broda, Małgorzata A
|e verfasserin
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|a Wieczorek, Piotr P
|e verfasserin
|4 aut
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|i Enthalten in
|t Magnetic resonance in chemistry : MRC
|d 1985
|g 58(2020), 6 vom: 15. Juni, Seite 584-593
|w (DE-627)NLM098179667
|x 1097-458X
|7 nnas
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|g volume:58
|g year:2020
|g number:6
|g day:15
|g month:06
|g pages:584-593
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|u http://dx.doi.org/10.1002/mrc.4990
|3 Volltext
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