Protecting group free synthesis of urea-linked glycoconjugates: efficient synthesis of β-urea glycosides in aqueous solution

Org Biomol Chem. 2014 Jun 21;12(23):3924-31. doi: 10.1039/c3ob42452a.

Abstract

A method for the protecting group free synthesis of β-urea-linked glycoconjugates has been developed. The one step process, involving reactions between urea and D-glucose, N-acetyl-D-glucosamine or D-xylose in acidic aqueous solution, furnishes the corresponding β-urea glycosides in modest yields. This simple and efficient procedure is applicable to the synthesis of β-urea tethered amino acid-carbohydrate conjugates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Glycoconjugates / chemical synthesis*
  • Glycoconjugates / chemistry
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Glycosylation
  • Proton Magnetic Resonance Spectroscopy
  • Solutions
  • Urea / chemistry*

Substances

  • Glycoconjugates
  • Glycosides
  • Solutions
  • xylosides
  • Urea