Synthesis of some cluster galactosides and their effect on the hepatic galactose-binding system

Kitchitaro Kawaguchi, Mark Kuhlenschmidt, Saul Roseman, Yuan Chuan Lee

Research output: Contribution to journalArticlepeer-review

Abstract

Mono-, bis-, and tris-β-d-galactopyranosides of (2-(5-hydrazinocarbonylpentanamido)-2-(hydroxymethyl)-1, 3-propanediol were synthesized. Treatment of the glycosides with nitrous acid gave the corresponding acyl azides which were coupled to bovine serum albumin to form neoglycoproteins. These derivatives were tested for their inhibitory action on (i) the d-galactose binding by rabbit liver membrane, (ii) the corresponding binding by the isolated binding protein, and (iii) the corresponding uptake by intact rat hepatocytes. In these systems, the neoglycoprotein with attached tris-galacto was a better inhibitor than the bis derivative, which in turn was more effective than the mono derivative per each ligand. However, the order is reversed when the inhibitory action is expressed on the basis of d-galactosyl residue.

Original languageEnglish (US)
Pages (from-to)388-395
Number of pages8
JournalArchives of Biochemistry and Biophysics
Volume205
Issue number2
DOIs
StatePublished - Dec 1980
Externally publishedYes

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology

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