'Click chemistry' on polysaccharides: a convenient, general, and monitorable approach to develop (1-->3)-beta-D-glucans with various functional appendages

Carbohydr Res. 2006 Jan 16;341(1):35-40. doi: 10.1016/j.carres.2005.10.009. Epub 2005 Nov 14.

Abstract

(1-->3)-beta-D-Glucans having various functional appendages (lactoside, ferrocene, pyrene, and porphyrin) can be prepared in an convenient, quantitative, and regioselective manner through regioselective bromination-azidation of curdlan to afford 6-azido-6-deoxycurdlan followed by chemoselective [3+2]-cycloadditions with various functional modules bearing a terminal alkyne group. The ability to monitor reaction conversions is an additional advantage of this synthetic approach over the conventional direct modifications on polysaccharides; the reaction can be readily monitored based on the intensity of azido peaks in the in situ attenuated total reflection infrared spectra.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Azides / chemistry
  • Nuclear Magnetic Resonance, Biomolecular
  • Proteoglycans
  • Spectroscopy, Fourier Transform Infrared
  • beta-Glucans / chemical synthesis*
  • beta-Glucans / chemistry

Substances

  • Alkynes
  • Azides
  • Proteoglycans
  • beta-Glucans
  • polysaccharide-K
  • curdlan