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Monosaccharides as Potential Chiral Probes for the Determination of the Absolute Configuration of Secondary Alcohols

2016; American Chemical Society; Volume: 79; Issue: 11 Linguagem: Inglês

10.1021/acs.jnatprod.6b00471

1520-6025

Tomasz Laskowski, Katarzyna Szwarc, Paweł Szczeblewski, Paweł Sowiński, E. Borowski, Jan Pawlak,

Metabolomics and Mass Spectrometry Studies

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 the 1H 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.