Synthesis of phenyl 6′-O-malonyl-β-D-glucopyranoside. Facile preparation of malonylated glycoconjugates

René Röscher, Jens Peter Steifen, Markus Herderich, Wilfried Schwab, Peter Schreier

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11 Scopus citations

Abstract

Regioselective acylation of glycoconjugates with malonic acid was achieved by using phenyl β-D-glucopyranoside as a model glycoside, malonic acid, and tert-butyl isocyanide in aprotic solvents. Structural elucidation of phenyl 6′-O-malonyl-β-D-glucopyranoside was performed by 1H and 13C NMR spectroscopy and high-performance liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry (HPLC-APCI-MS/MS). This one-step reaction opens the way to the preparation of reference substances which are required for the spectroscopic identification of malonylated glycosides in complex natural matrices.

Original languageEnglish
Pages (from-to)1626-1629
Number of pages4
JournalJournal of agricultural and food chemistry
Volume44
Issue number7
DOIs
StatePublished - 1996
Externally publishedYes

Keywords

  • Atmospheric pressure chemical ionization (APCI)
  • HPLC-MS/MS
  • Malonylated glycosides
  • Phenyl 6′-O-malonyl-β-D-glucopyranoside

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