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pubmed-article:6321733pubmed:abstractTextA 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.lld:pubmed
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pubmed-article:6321733pubmed:dateRevised2007-11-15lld:pubmed
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pubmed-article:6321733pubmed:articleTitleCardiac glycosides. 1. A systematic study of digitoxigenin D-glycosides.lld:pubmed
pubmed-article:6321733pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:6321733pubmed:publicationTypeResearch Support, U.S. Gov't, P.H.S.lld:pubmed
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