Monatshefte für Chemie - Chemical Monthly

, Volume 144, Issue 2, pp 255–262

Glucosides of morphine derivatives: synthesis and characterization

  • András Váradi
  • Dóra Lévai
  • Gergő Tóth
  • Péter Horváth
  • Béla Noszál
  • Sándor Hosztafi
Original Paper

Abstract

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.

Graphical Abstract

Keywords

Morphine Glucoside NMR spectroscopy Alkaloids High-pressure liquid chromatography 

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Copyright information

© Springer-Verlag Wien 2012

Authors and Affiliations

  • András Váradi
    • 1
  • Dóra Lévai
    • 1
  • Gergő Tóth
    • 1
  • Péter Horváth
    • 1
  • Béla Noszál
    • 1
  • Sándor Hosztafi
    • 1
  1. 1.Department of Pharmaceutical ChemistrySemmelweis UniversityBudapestHungary

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