A new homobifunctional p-nitro phenyl ester coupling reagent for the preparation of neoglycoproteins

Org Lett. 2004 Nov 25;6(24):4407-10. doi: 10.1021/ol048614m.

Abstract

A new linker system has been designed and applied to neoglycoprotein synthesis. Reaction of oligosaccharide omega-aminoalkyl glycosides with homobifunctional adipic acid p-nitrophenyl diesters in dry DMF gave the corresponding amide half ester in good yields and of sufficient stability to permit chromatographic purification. Subsequent conjugation with bovine serum albumin under very mild conditions afforded the corresponding neoglycoproteins with good efficiency. The method is well suited for the coupling of very small amounts (mg) of oligosaccharide and protein. [structure: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides
  • Cross-Linking Reagents / chemistry*
  • Esters / chemistry
  • Glycoproteins / chemical synthesis*
  • Nitrophenols / chemistry*
  • Oligosaccharides / chemistry

Substances

  • Amides
  • Cross-Linking Reagents
  • Esters
  • Glycoproteins
  • Nitrophenols
  • Oligosaccharides