Probe design and synthesis of Galbeta(1-->3)[NeuAcalpha(2-->6)]GlcNAcbeta(1-->2)Man motif of N-glycan

Bioorg Med Chem. 2010 Jun 1;18(11):3760-6. doi: 10.1016/j.bmc.2010.04.067. Epub 2010 Apr 28.

Abstract

Synthesis and clusterization of Galbeta(1-->3)[NeuAcalpha(2-->6)]GlcNAcbeta(1-->2)Man motif of the N-glycan, as the molecular probes for their biological evaluation, are reported. Key step is the quantitative and the completely alpha-selective sialylation of the C5-azide N-phenyltrifluoroacetimidate with the disaccharide acceptor, Galbeta(1-->3)GlcNTroc. Clusterization of the 16 molecules of trisaccharide motif was also achieved by the 'self-activating click reaction'. These probes could efficiently be labeled by biotin and/or other fluorescence- or radioactive reporter groups through either cross metathesis, acylation, Cu(I)-mediated Huisgen [2+3]-cycloaddition, or the azaelectrocyclization to utilize the various biological techniques.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Molecular Probes / chemical synthesis*
  • Polysaccharides / chemical synthesis*
  • Polysaccharides / chemistry

Substances

  • Molecular Probes
  • Polysaccharides