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1 H and 13 C NMR study of quaternary benzo[ c ]phenanthridine alkaloids 1
Author(s) -
Marek Radek,
Toušek Jaromír,
Dostál Jiří,
Slavík Jiří,
Dommisse Roger,
Sklenář Vladimír
Publication year - 1999
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199911)37:11<781::aid-mrc556>3.0.co;2-h
Subject(s) - phenanthridine , chemistry , sanguinarine , chemical shift , ab initio , nuclear magnetic resonance spectroscopy , computational chemistry , carbon 13 nmr , chelerythrine , stereochemistry , alkaloid , organic chemistry , protein kinase c , enzyme
1 H, 13 C and in some cases also 15 N chemical shifts of quaternary benzo[ c ]phenanthridine alkaloids (fagaronine, chelerythrine, chelilutine, chelirubine, nitidine, sanguilutine, sanguinarine, and sanguirubine) were systematically studied by NMR spectroscopy and ab initio calculations. The assignment of signals in the 1 H and 13 C NMR spectra was obtained from 2D NOE and gradient‐enhanced single‐quantum multiple bond correlation (GSQMBC) experiments. The ab initio geometry optimization using Gaussian 94 at the RHF/6–31 G** level, followed by the calculation of chemical shielding using the deMon/NMR code at the IGLO II level, were carried out in order to rationalize the assignment of individual experimentally determined resonances. Copyright © 1999 John Wiley & Sons, Ltd.