Glucosides of morphine derivatives: synthesis and characterization
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- Váradi, A., Lévai, D., Tóth, G. et al. Monatsh Chem (2013) 144: 255. doi:10.1007/s00706-012-0868-4
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Six 3-O- and 6-O-glucosides of morphine and codeine derivatives were synthesized by means of glucosylation with acetobromo-α-d-glucose. O-Glucosylation at C6 was carried out by the Koenigs-Knorr method, whereas the 3-O-glycoside of morphine was synthesized directly upon stirring morphine with acetobromo-α-d-glucose and aqueous sodium hydroxide in acetone. Complete 1H and 13C NMR assignments are presented for each synthesized compound based on one- and two-dimensional homo- and heteronuclear NMR techniques. Circular dichroism, ultraviolet absorbance, and high-resolution mass spectroscopy data ensure identification and structural characterization of the O-glucoside conjugates. The synthesized glucoside conjugates are potential analgesics; the presented spectral and chromatographic data are useful references for various analytical and metabolic studies including samples of biological origin.