Synthesis of D-galactosamine derivatives and binding studies using isolated rat hepatocytes

Ting Chi Wong, R. Reid Townsend, Yuan Chuan Lee

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

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-β-D-galactopyranoside, 6-amino-hex-1-yl 2-deoxy-2-(trifluoroacetamido)-β-D-galactopyranoside, the mono- and di-O-methyl derivatives of allyl 2-acetamido-2-deoxy-β-D-galactopyranoside, and allyl 2-acetamido-2,4-dideoxy-4-fluoro-α-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.

Original languageEnglish
Pages (from-to)27-46
Number of pages20
JournalCarbohydrate Research
Volume170
Issue number1
DOIs
StatePublished - Dec 1 1987
Externally publishedYes

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