Synthesis of glycopeptides and neoglycoproteins containing the fucosylated linkage region of N-glycoproteins

Bioorg Med Chem. 1994 Nov;2(11):1189-201. doi: 10.1016/s0968-0896(00)82070-2.

Abstract

N-Glycoproteins fucosylated in the core region occur in tumor membranes and virus envelopes. Partial structures of such N-glycoproteins containing fucosylated chitobiosyl asparagine conjugates were synthesized using the allyloxycarbonyl (Aloc) and the tert-butyl ester protecting groups in the peptide portion. As the alpha-fucosidic bond of the conjugates revealed to be very sensitive to acids when carrying ether-type protecting groups, a method for exchanging the protecting groups of the fucose portion of saccharides was developed. Conjugates containing O-acetyl protected fucose proved to be stable against acids used in glycopeptide syntheses. These methods were applied in the synthesis of a fucosyl chitobiose hexapeptide with the partial sequence of a leukemia virus envelope glycoprotein. The glycopeptide was coupled to bovine serum albumin yielding a neoglycoprotein which contains a glycoconjugate of exactly specified structure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Asparagine / chemistry
  • Carbohydrate Sequence
  • Disaccharides*
  • Fucose / chemistry*
  • Fucosyltransferases / metabolism
  • Glucans / chemistry
  • Glycopeptides / chemical synthesis*
  • Glycoproteins / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Viral Proteins / chemistry

Substances

  • Disaccharides
  • Glucans
  • Glycopeptides
  • Glycoproteins
  • Viral Proteins
  • Fucose
  • chitobiose
  • Asparagine
  • Fucosyltransferases