Block synthesis of tetra- and hexasaccharides (beta-D-glycero-D-manno-Hep p-(1-->4)-[alpha-l-Rha p-(1-->3)-beta-D-glycero-D-manno-Hep p-(1-->4)]n-alpha-L-Rha p-OMe (n = 1 and 2)) corresponding to multiple repeat units of the glycan from the surface-layer glycoprotein from Bacillus thermoaerophilus

J Org Chem. 2008 Sep 19;73(18):7003-10. doi: 10.1021/jo801414c. Epub 2008 Aug 27.

Abstract

A fully stereocontrolled block synthesis of the title tetra- and hexasaccharides has been achieved taking advantage of the ability of the 4,6-O-benzylidene acetal to control the stereochemistry of the beta-D-glycero-D-mannoheptopyranoside unit and of a 2,3-O-diphenylmethylene acetal to install the alpha-L-rhamnopyranosidic linkages. Comparison of the spectral data for the hexasaccharide with that of the natural isolate confirms the structure of this very unusual and structurally challenging glycan.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Bacillus / chemistry*
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Glycoproteins / chemistry*
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Polysaccharides / chemistry*

Substances

  • Glycoproteins
  • Oligosaccharides
  • Polysaccharides