dc.contributor.author |
Kraszni, Marta |
|
dc.contributor.author |
Kokosi, Jozsef |
|
dc.contributor.author |
Noszal, Bela |
|
dc.date.accessioned |
2023-05-26T10:01:20Z |
|
dc.date.available |
2023-05-26T10:01:20Z |
|
dc.date.issued |
2002 |
|
dc.identifier |
0036014017 |
|
dc.identifier.citation |
journalIssueNumber=5;journalTitle=JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2;pagerange=914-917;journalAbbreviatedTitle=J CHEM SOC PERKIN TRANS 2; |
|
dc.identifier.uri |
http://repo.lib.semmelweis.hu//handle/123456789/9440 |
|
dc.identifier.uri |
doi:https://doi.org/10.1039/b200846g |
|
dc.description.abstract |
A method was developed and applied to determine the populations and site- and conformer-specific basicities of histamine rotamers in three distinct states of protonation. The method that has been developed also allows the determination of molecule- and position-specific standard gauche and trans H-1 NMR coupling constants, and the subsequent rotamer analysis from NMR spin systems with a single observed coupling constant, introducing simplifying allowances of symmetry origin. Synthesis and NMR analysis of a reference histamine derivative have also been carried out. The trans rotamers of histamine were found to exist in 41, 38 and 50% in the neutral, monocationic and dicationic forms, respectively, providing quantitative, experimental evidence for the preferential thermodynamic properties of the trans species over the two enantiomeric, statistically favoured g conformers in any ionisation form. Quanti cation of the rotamer- and site- specific basicities resulted in increased amino and decreased imidazole basicities in the gauche rotamer, indicating the formation of intramolecular hydrogen bonds in the monocationic form. |
|
dc.format.extent |
914-917 |
|
dc.title |
Concentration and basicity of histamine rotamers |
|
dc.type |
Journal Article |
|
dc.date.updated |
2023-05-11T13:43:26Z |
|
dc.language.rfc3066 |
en |
|
dc.rights.holder |
NULL |
|
dc.identifier.mtmt |
1478240 |
|
dc.identifier.wos |
000175325400010 |
|
dc.contributor.department |
SE/GYTK/Gyógyszerészi Kémiai Intézet |
|
dc.contributor.institution |
Semmelweis Egyetem |
|