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Complete 1H and 13C NMR assignments for apramycin, sisomicin and some N- and N,O-polyacetylated aminoglycosides

✍ Scribed by Galya I. Eneva; Stefan L. Spassov; Marietta A. Haimova; Jan Sandström

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
533 KB
Volume
30
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

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.

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