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Complete 1 H and 13 C NMR assignments for apramycin, sisomicin and some N ‐ and N , O ‐polyacetylated aminoglycosides
Author(s) -
Eneva Galya I.,
Spassov Stefan L.,
Haimova Marietta A.,
Sandström Jan
Publication year - 1992
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.1260300908
Subject(s) - sisomicin , chemistry , coupling constant , nuclear magnetic resonance spectroscopy , tobramycin , chemical shift , stereochemistry , ring (chemistry) , crystallography , antibiotics , organic chemistry , gentamicin , biochemistry , physics , particle physics
The 1 H NMR spectra (300 MHz) of the aminoglycoside antibiotics apramycin and sisomicin (free bases) were completely analysed by 1D and 2D methods (mainly 1 H 1 H and 1 H 13 C shift‐correlation spectroscopy). The complete 1 H nd 13 C NMR assignment of a series of semisynthetic N ‐polyacetyl‐ and N , O ‐polyacetyl derivatives of kanamycins A and B, tobramycin, apramycin and sisomicin was also achieved via these techniques. The effect of acetylation on the 1 H and 13 C chemical shifts, 1 H 1 H coupling constants and ring conformations is discussed. The vicinal coupling constants for the unsaturated ring in sisomicin, calculated on the basis of the energetically favoured conformation predicated by the MMP2 method, are in good agreement with the experimental data.