Interunit, through-space 1H-19F and 13C-19F spin-spin couplings of 5-fluorinated arbekacins.
5-Deoxy-5-fluoroarbekacin (1) and 5-deoxy-5,5-difluoroarbekacin (2) showed interunit, through-space 1H-19F spin-spin couplings at the signals for H-1', 4", 5", 6"a and 6"b with F-5eq. These couplings were detected by a new NMR method, 1H-detected 2D 1H-19F chemical shift correlation spectroscopy. These two compounds also displayed interunit, through-space 13C-19F couplings at the resonances for C-1' and 5" with F-5eq. These couplings were corroborated by 1D 13C[1H]-[19F] triple-resonance techniques. Triple-resonance 13C-19F COSY experiments were also carried out. The interunit conformational information obtained with the through-space 1H-19F and 13C-19F couplings was further supported by heteronuclear 1H[19F] NOE experiments.
Institute of Bioorganic Chemistry, Kawasaki, Japan.
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Miyake
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Koyama
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002247:Carbon Isotopes; D003982:Dibekacin / Q000031:analogs & derivatives* / Q000737:chemistry*; D005462:Fluorine Radioisotopes; D006859:Hydrogen; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D013329:Structure-Activity Relationship
D002247:Carbon Isotopes; D005462:Fluorine Radioisotopes; C088550:5-deoxy-5-fluoroarbekacin; C088552:5-deoxy-5,5-difluoroarbekacin; D003982:Dibekacin; D006859:Hydrogen