Solid-phase synthesis of CD52 glycopeptide and an efficient route to Asn-core pentasaccharide conjugate

Bioorg Med Chem. 1997 Oct;5(10):1917-24. doi: 10.1016/s0968-0896(97)00126-0.

Abstract

The intact peptide sequence (18) as well as its glycoform carrying an N-linked core pentasaccharide (1) of CD52 antigen were prepared by means of solid-phase synthesis employing Fmoc-amino acids and benzyl-protected oligosaccharide-asparagine conjugate (3) as building blocks. It was concluded that the pentasaccharide structure had little influence on further peptide elongation in solid-phase synthesis and the benzylated pentasaccharide moiety was sufficiently stable to the 95% TFA acidic conditions used to release glycopeptide from the supporting resin. The paper also describes an efficient route leading to asparagine-core pentasaccharide conjugate (3) which was prepared in seven steps for an overall yield of 23% from monosaccharide units 5, 6, 7 and 8.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antigens, CD / chemistry*
  • Antigens, Neoplasm*
  • Asparagine / chemistry
  • CD52 Antigen
  • Carbohydrate Sequence
  • Glycopeptides / chemical synthesis*
  • Glycoproteins / chemistry*
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Monosaccharides / chemistry
  • Structure-Activity Relationship

Substances

  • Antigens, CD
  • Antigens, Neoplasm
  • CD52 Antigen
  • CD52 protein, human
  • Glycopeptides
  • Glycoproteins
  • Monosaccharides
  • Asparagine