Abstract
Structure-activity relationships in the induction of strand breakage in plasmid pBR322 DNA by amino sugars and their derivatives were investigated using agarose gel electrophoresis. The coexistence of a potential free aldehyde group at the C-1 position and a free amino group at the C-2 position in the molecules was indispensable for the display of DNA strand-breaking activity in both mono- and oligo-aminosaccharides. The activity was increased by the introduction of an acidic group, especially a phosphate group, at the C-6 position. The activity was also increased by the addition of Cu 2+. The order of activity of the amino monosaccharides tested was d-isoglucosamine d-mannosamine d-galactosamine d-glucosamine, and it is suggested that this order is correlated with the portion of acyclic ( aldehydo) form in the solution of each sugar. The possible chemical basis for DNA strand breakage by amino sugars is discussed.
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