Synthesis of the sugar moiety of TIME-EA4, a glycopeptide isolated from silkworm diapause eggs

Carbohydr Res. 2006 Aug 14;341(11):1796-802. doi: 10.1016/j.carres.2006.04.015. Epub 2006 May 15.

Abstract

We describe the efficient synthesis of the tetrasaccharide, 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1-->6)-2,4-di-O-acetyl-3-O-allyl-beta-D-mannopyranosyl-(1-->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl-(1-->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl azide, which is the protected form of the sugar unit of TIME-EA4 that is isolated from the diapausing eggs of the silkworm, Bombyx mori. The beta-linked D-mannoside of the tetrasaccharide was obtained using the conventional oxidation-reduction method for inversion of the configuration at the C-2 hydroxyl group of beta-D-glucoside. The reduction was effected with NaBH(4) in a methanolic solution in a ratio of 98:2 in favor of the beta-D-mannoside that was obtained in 87% yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bombyx / chemistry*
  • Carbohydrate Sequence
  • Female
  • Glycopeptides / chemistry*
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Glycosylation
  • Magnetic Resonance Spectroscopy
  • Mannosides / chemistry
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Ovum / chemistry*
  • Oxidation-Reduction

Substances

  • 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1-6)-2,4-di-O-acetyl-3-O-allyl-beta-D-mannopyranosyl-(1-4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl-(1-4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl azide
  • Glycopeptides
  • Glycosides
  • Mannosides
  • Oligosaccharides