Journal
MAGNETIC RESONANCE IN CHEMISTRY
Volume 60, Issue 10, Pages 963-969Publisher
WILEY
DOI: 10.1002/mrc.5297
Keywords
1; 1-ADEQUATE; C-13; carbapenem; DFT; NMR; reassignment
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In this study, C-13 chemical shift of the β-lactam carbonyl at the C-7 position and the proximal carboxylate at the C-10 position in the carbapenems meropenem and imipenem were successfully reassigned using 1,1-ADEQUATE data. Density functional theory (DFT) was employed to accurately predict C-13 chemical shifts, facilitating the reassignment of the carbonyl signal in thienamycin.
Prior to the development of sensitive proton-detected 2D NMR experiments, assigning C-13 signals could be a significant challenge, and mistakes have occurred even for prominent compound classes. In this study, 1,1-ADEQUATE data were used to unambiguously reassign the C-13 chemical shifts for the beta-lactam carbonyl at the C-7 position and the proximal carboxylate at the C-10 position of the carbapenems, meropenem and imipenem. Density functional theory (DFT) was then investigated to provide sufficiently accurate C-13 chemical shift predictions, allowing for the carbonyl signal reassignment of thienamycin.
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