Application of the 2-deoxyglucose scaffold as a new chiral probe for elucidation of the absolute configuration of secondary alcohols

Abstract

Herein, we present the application of 2-deoxy-d-glucose derivatives as chiral probes for elucidation of the absolute configuration of chiral secondary alcohols. The probes are attached to the studied molecules via glycosylation reaction and the resulting products are examined by a set of standard 2D NMR experiments. The absolute configuration of an oxymethine carbon atom binding the probe is established on a basis of a set of diagnostic dipolar couplings (NOEs/ROEs). These correlations may be considered diagnostic due to a pronounced lack of conformational freedom of the formed glycosidic linkage. While the chance for an observation of the diagnostic signals is the highest when the resulting glycoside in an α-anomer. 2-deoxy-d-glucose was selected as a probe of choice since is it known to strongly prefer the formation of α-glycosides

19F NMR enantiodiscrimination and diastereomeric purity determination of amino acids, dipeptides, and amines

“…Chiral amino-group compounds are not only important biomolecules but also chemical and pharmaceutical intermediates for the synthesis of bioactive compounds. Currently, various methods have been widely used for the elucidation of absolute configuration and enantiomeric excess (ee), including NMR, [1][2][3][4][5][6][7][8][9][10][11][12] circular dichroism, [13][14][15][16][17] fluorescence, 18 SERS, 19 chromatography, 20,21 ion mobility mass spectrometry, 22 and electrochemistry. 23,24 However, optical spectroscopic techniques require pure enantiomers that are obtained by isolating each enantiomeric pair or by extracting each enantiomer from its original matrix prior to analysis.…”