PT  - JOURNAL ARTICLE
AU  - N Hirayama
AU  - K Shirahata
AU  - Y Ohashi
AU  - Y Sasada
TI  - Conformations of fortimicins and three-dimensional structure-activity relationship in the aminoglycoside antibiotics.
DP  - 1983 Jan 01
TA  - Molecular Pharmacology
PG  - 127--132
VI  - 23
IP  - 1
4099  - http://molpharm.aspetjournals.org/content/23/1/127.short
4100  - http://molpharm.aspetjournals.org/content/23/1/127.full
SO  - Mol Pharmacol1983 Jan 01; 23
AB  - The fortimicins are pseudodisaccharide antibiotics consisting of purpurosamine and fortamine moieties which are connected through an alpha-linkage. NMR spectra indicate that the fortamine ring in fortimicin A takes a chair conformation which corresponds to an inverted one in the conformation of fortimicin B free base. Fortimicin A is unstable in solution, and we were unable to obtain any crystals of it. To elucidate the structure of fortimicin A and to clarify the stereochemistry of fortimicins, we have undertaken to calculate their empirical force-fields starting from the X-ray structures of fortamines and fortimicin B free base. Nuclear Overhauser enhancement data were also employed to confirm the calculated relative orientation of the two rings around the glycosidic linkage. The 3-dimensional structure-activity relationship of aminoglycoside antibiotics is discussed on the basis of these results.