Efficient synthesis of methyl lycotetraoside, the tetrasaccharide constituent of the tomato defence glycoalkaloid alpha-tomatine

Org Biomol Chem. 2005 Sep 7;3(17):3201-6. doi: 10.1039/b508752j. Epub 2005 Jul 27.

Abstract

Branched oligosaccharide lycotetraose, beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranose, is a key constituent of many steroidal saponins, including glycoalkaloid alpha-tomatine, which is involved in protection of plants from invading pathogens. A new synthesis of the methyl beta-lycotetraoside () is described. Key steps of the synthesis include two successive glycosylation reactions of disaccharide acceptor methyl (4,6-O-benzylidene-3-O-p-methoxybenzyl-beta-D-glucopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-beta-D-galactopyranoside with readily available benzoylated trichloroacetimidates of alpha-D-glucopyranose and alpha,beta-D-xylopyranose. This scheme allows sequential glycosylation in one-pot on account of the convenient in situ removal of a p-methoxybenzyl protecting group under the acid conditions of the first glycosylation step. Following deprotection, tetrasaccharide was obtained in 19% yield over eight steps.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Glycosylation
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*
  • Solanum lycopersicum / chemistry*
  • Tomatine / analogs & derivatives*
  • Tomatine / chemistry*

Substances

  • Oligosaccharides
  • methyl lycotetraoside
  • Tomatine