A carbon-13 nuclear magnetic resonance study of solid tetracyclines

Abstract

Magic angle sample spinning and proton/carbon-13 cross-polarization techniques have been used to obtain high resolution solid state 13C nuclear magnetic resonance spectra of several tetracycline antibiotics. Carbon-13 resonances in the solid state are assigned by measuring the extent of dipolar broadening due to neighbouring quadrupolar nuclei and by using a pulse sequence that suppresses non-quaternary carbon resonances. The observed 13C chemical shifts are discussed in light of the known solid state structures derived from X-ray diffraction, and are compared with those in solution. It is shown that the solid state nuclear magnetic reosnance technique is capable of clearly distinguishing between the neutral and zwitterionic forms of the tetracycline free bases.