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Different solution and solid‐state conformations of the antibiotic cycloheximide
Author(s) -
Perry Nigel B.,
Blunt John W.,
Munro Murray H. G.
Publication year - 1989
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.1260270704
Subject(s) - chemistry , cycloheximide , hydrogen bond , cyclohexanone , solid state , nmr spectra database , coupling constant , planarity testing , spectral line , stereochemistry , computational chemistry , crystallography , molecule , organic chemistry , protein biosynthesis , biochemistry , physics , particle physics , astronomy , catalysis
The 1 H NMR spectra of the antibiotic cycloheximide in CDCl 3 and CD 3 OD have been assigned. Analyses of coupling constants and difference NOE spectra showed different conformations in these two solvents, due to changeover between intra‐ and inter‐molecular hydrogen bonding. The twist boat cyclohexanone found in the solid state was not detected in solution. The results are compared with the solution and solid‐state conformations of the antitumour agent sesbanimide A.