Synthesis of a sialic acid alpha(2-3) galactose building block and its use in a linear synthesis of sialyl Lewis X

Org Lett. 2007 Apr 26;9(9):1777-9. doi: 10.1021/ol0704946. Epub 2007 Apr 6.

Abstract

[reaction: see text] The ubiquity of the sialic acid alpha(2-3) galactose linkage in oligosaccharides of biological relevance necessitates a building block for the incorporation of this motif into oligosaccharides prepared by modular synthesis. The linear synthesis of the sialyl Lewis X tumor-associated antigen (1) has been accomplished in good yield using a sialic acid alpha(2-3) galactose disaccharide building block. The disaccharide building block was synthesized efficiently from readily available galactal by a high-yielding and selective sialylation reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Galactose / chemistry
  • Glycosylation
  • Molecular Structure
  • N-Acetylneuraminic Acid / chemical synthesis*
  • N-Acetylneuraminic Acid / chemistry
  • Oligosaccharides / chemistry*
  • Sialyl Lewis X Antigen

Substances

  • Oligosaccharides
  • Sialyl Lewis X Antigen
  • N-Acetylneuraminic Acid
  • Galactose