TY - JOUR
T1 - Synthesis of some cluster galactosides and their effect on the hepatic galactose-binding system
AU - Kawaguchi, Kitchitaro
AU - Kuhlenschmidt, Mark
AU - Roseman, Saul
AU - Lee, Yuan Chuan
N1 - Funding Information:
’ Contribution No. 1070 from the McCollum-Pratt Institute, The Johns Hopkins University. Supported by USPHS National Institutes of Health Research Grants AM9970 and CA21901.
PY - 1980/12
Y1 - 1980/12
N2 - 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.
AB - 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.
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U2 - 10.1016/0003-9861(80)90121-6
DO - 10.1016/0003-9861(80)90121-6
M3 - Article
C2 - 7469417
AN - SCOPUS:0019248962
SN - 0003-9861
VL - 205
SP - 388
EP - 395
JO - Archives of Biochemistry and Biophysics
JF - Archives of Biochemistry and Biophysics
IS - 2
ER -