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Monosaccharides as internal probes for the determination of the absolute configuration of 2‐butanol
Author(s) -
Seroka Patrycja,
Płosiński Marcin,
Czub Jacek,
Sowiński Paweł,
Pawlak Jan
Publication year - 2006
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1735
Subject(s) - chemistry , heteronuclear molecule , two dimensional nuclear magnetic resonance spectroscopy , absolute configuration , glycoside , glycosidic bond , rhamnose , monosaccharide , stereochemistry , nuclear overhauser effect , 2 butanol , analytical chemistry (journal) , nuclear magnetic resonance spectroscopy , butanol , mannose , organic chemistry , ethanol , enzyme
D ‐Glucose, D ‐mannose and L ‐rhamnose were reacted with a racemic mixture of 2‐butanol, and the resulting α‐glycosides were analyzed by 1 H NMR with COSY and NOESY experiments. Conformational analysis of α‐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 α‐glycosides. Copyright © 2005 John Wiley & Sons, Ltd.