Convenient conversion of wheat hemicelluloses pentoses (D-xylose and L-arabinose) into a common intermediate

Carbohydr Res. 2007 Nov 26;342(16):2450-5. doi: 10.1016/j.carres.2007.07.010. Epub 2007 Jul 21.

Abstract

The transformation of D-xylose and L-arabinose, the two major components of wheat straw and bran, into a unique multifunctional, optically pure, five-carbon synthon has been achieved. The synthetic sequence requires three steps: suitable protection of the hydroxyl groups of the pentoses, introduction of an iodide at the C-5 position and zinc-mediated opening of the furanose ring leading to the formation of a common substituted pent-4-enal.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arabinose / chemistry*
  • Molecular Structure
  • Polysaccharides / chemistry*
  • Triticum / chemistry*
  • Xylose / chemistry*

Substances

  • Polysaccharides
  • hemicellulose
  • Xylose
  • Arabinose