title: Monosaccharides as Potential Chiral Probes for the Determination of the Absolute Configuration of Secondary Alcohols.
abstract: Herein, a new method for the elucidation of the absolute configuration of chiral secondary alcohols is proposed. This method is an alternative for a widely used approach reported by Mosher and Dale and similar methods that are based on the1H NMR shift (δ) changes of protons that are attached to the substituents of the oxymethine carbon atom. The presented method is not based on tracking the chemical shift changes and utilizes stereochemically defined monosaccharides as chiral probes. A secondary alcohol is glycosylated, and the resulting glycoside is subjected to NMR studies. The observation of dipolar couplings between the protons of the monosaccharide moiety and the protons of the secondary alcohol moiety via the NOESY/ROESY spectra enables the determination of the absolute configuration of the oxymethine carbon atom.
authors: Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdańsk University of Technology , Gabriela Narutowicza Street 11/12, 80-233 Gdańsk, Poland.
authors: Tomasz
authors: T
authors: Laskowski
authors: Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdańsk University of Technology , Gabriela Narutowicza Street 11/12, 80-233 Gdańsk, Poland.
authors: Katarzyna
authors: K
authors: Szwarc
authors: Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdańsk University of Technology , Gabriela Narutowicza Street 11/12, 80-233 Gdańsk, Poland.
authors: Paweł
authors: P
authors: Szczeblewski
authors: Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdańsk University of Technology , Gabriela Narutowicza Street 11/12, 80-233 Gdańsk, Poland.
authors: Paweł
authors: P
authors: Sowiński
authors: Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdańsk University of Technology , Gabriela Narutowicza Street 11/12, 80-233 Gdańsk, Poland.
authors: Edward
authors: E
authors: Borowski
authors: Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdańsk University of Technology , Gabriela Narutowicza Street 11/12, 80-233 Gdańsk, Poland.
authors: Jan
authors: J
authors: Pawlak
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D004952:Esters; D006027:Glycosides / Q000737:chemistry; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D011522:Protons; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D004952:Esters; D006027:Glycosides; D009005:Monosaccharides; D011522:Protons