Monosaccharides as internal probes for the determination of the absolute configuration of 2-butanol |
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| Authors: | Seroka Patrycja P?osiński Marcin Czub Jacek Sowiński Pawe? Pawlak Jan |
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| Institution: | Department of Pharmaceutical Technology and Biochemistry, Gdańsk University of Technology, 80-952 Gdańsk, Poland. |
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| Abstract: | 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. |
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| Keywords: | 1H NMR COSY NOESY monosaccharides chiral probe secondary alcohols stereochemistry |
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