✦ LIBER ✦

1H and 13C NMR studies of aminoglycoside antibiotics

✍ Scribed by Gerard P. Moloney; David J. Craik; Magdy N. Iskander

Publisher: John Wiley and Sons
Year: 1993
Tongue: English
Weight: 640 KB
Volume: 31
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1260311209

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✦ Synopsis

Abstract

^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.

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