Synthesis of D-galactosamine derivatives and binding studies using isolated rat hepatocytes.
Derivatives of glycosides of D-galactosamine were prepared in order to study further the binding requirement of the Gal/GalNAc receptor in mammalian hepatocytes. These structures included N-propanoyl, N-benzoyl, and N,N-phthaloyl derivatives of 2-hydroxyethyl 2-amino-2-deoxy-beta-D-galactopyranoside, 6-amino-hex-1-yl 2-deoxy-2-(trifluoroacetamido)-beta-D-galactopyranoside, the mono- and di-O-methyl derivatives of allyl 2-acetamido-2-deoxy-beta-D-galactopyranoside, and allyl 2-acetamido-2,4-dideoxy-4-fluoro-alpha-D-galactopyranoside. The inhibition results confirmed some of our previous findings on the involvement of the hydroxyl groups, and provided new information on the involvement of the N-substituent, as well as on the requirement of hydrogen bonding of the 4-hydroxyl group in binding.
Wong
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TC
Department of Biology, Johns Hopkins University, Baltimore, Maryland 21218.
Townsend
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RR
Lee
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YC
D000818:Animals; D037263:Asialoglycoprotein Receptor; D001212:Asialoglycoproteins; D001667:Binding, Competitive; D005688:Galactosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D007700:Kinetics; D008099:Liver / Q000276:immunology / Q000378:metabolism*; D009961:Orosomucoid / Q000031:analogs & derivatives / Q000378:metabolism; D051381:Rats; D011971:Receptors, Immunologic / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship
D037263:Asialoglycoprotein Receptor; D001212:Asialoglycoproteins; D007202:Indicators and Reagents; D009961:Orosomucoid; D011971:Receptors, Immunologic; C017030:asialoorosomucoid; D005688:Galactosamine