Monosaccharides as internal probes for the determination of the absolute configuration of 2-butanol.
D-Glucose, D-mannose and L-rhamnose were reacted with a racemic mixture of 2-butanol, and the resulting alpha-glycosides were analyzed by 1H NMR with COSY and NOESY experiments. Conformational analysis of alpha-glycosidic bonds performed with molecular modeling and appropriate heteronuclear long-range coupling measurements and combined with analysis of dipolar couplings observed in NOESY spectra allowed the assignment of absolute configuration in the aglycones of elucidated alpha-glycosides.
Seroka
Patrycja
P
Department of Pharmaceutical Technology and Biochemistry, Gdańsk University of Technology, 80-952 Gdańsk, Poland.
Płosiński
Marcin
M
Czub
Jacek
J
Sowiński
Paweł
P
Pawlak
Jan
J
D000440:Butanols / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*
D000440:Butanols; D009005:Monosaccharides; C043958:2-butanol