| Literature DB >> 6321733 |
D S Fullerton, M Kihara, T Deffo, E Kitatsuji, K Ahmed, B Simat, A H From, D C Rohrer.
Abstract
A series of digitoxigenin glycosides was studied: five with beta-D-sugars varying stepwise in sugar structure from beta-D-digitoxose to beta-D-galactose, including one beta-D/alpha-D pair. I50 values for these glycosides and digitoxigenin were determined with hog kidney Na+, K+-ATPase. These data suggest a major and unexpected role for 4'-OH conformation in the sugar. All the glycosides with an equatorial 4'-OH were more active than the two with the 4'-OH axial [digitoxigenin beta-D-galactoside (6) I50 = 6.45 X 10(-8) M; digitoxigenin 2'-deoxy-alpha-D-ribo-hexopyranoside (alpha-3a) I50 = 9.33 X 10(-8) M; digitoxigenin I50 = 1.17 X 10(-7) M]. Stereochemistry of the 3'-OH had much less of an activity role than that of the 4'-OH, in contrast to existing models of "sugar-site" binding.Entities:
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Year: 1984 PMID： 6321733 DOI： 10.1021/jm00369a004
Source DB: PubMed Journal: J Med Chem ISSN： 0022-2623 Impact factor: 7.446