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1 H and 13 C NMR studies of aminoglycoside antibiotics
Author(s) -
Moloney Gerard P.,
Craik David J.,
Iskander Magdy N.
Publication year - 1993
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/mrc.1260311209
Subject(s) - chemistry , aqueous solution , ring (chemistry) , aminoglycoside , nuclear magnetic resonance spectroscopy , nuclear overhauser effect , benzaldehyde , stereochemistry , chemical shift , vicinal , computational chemistry , antibiotics , organic chemistry , biochemistry , catalysis
1 H NMR spectroscopy was used to determine the conformations of the aminoglycoside antibiotic N ‐demethylclindamycin and two of its cyclic derivatives. The conformational features of these systems were determined by consideration of vicinal coupling constants and, in some cases, nuclear Overhauser enhancement (NOE) effects. 1 H and 13 C chemical shifts are reported and compared with previous results for the related antibiotic lincomycin. The stability of the two cyclized derivatives in aqueous solution was examined. Both cyclizations involved formation of a 4‐imidazolidinone ring. It was found that the ring system based on cyclization with formaldehyde was stable in aqueous solution, whereas that based on benzaldehyde was not.