Biological Activity of Ribose-Modified N6-(Δ2-Isopentenyl)adenosine Derivative

Abstract
An analog of N6-(Δ2-isopentenyl)adenosine, 2-O-(1R-(9-N6-(Δ2-isopentenyI)adenyl)-2-hydroxyethyl) glycerol was prepared by cleavage of the 2′, 3′ carbon–carbon bond of the ribose moiety of N6-(Δ2-isopentenyl)adenosine by the technique of periodate oxidation and borohydride reduction of the dialdehyde to the diol. The net rate of uptake of this analog by tobacco-pith tissue cultures was about 40% of the N6-(Δ2-isopentenyl) [8-14C]-adenosine. The enzymatic hydrolysis of the glycosidic bond of this analog was not detected, but the N6-isopentenyl side chain was modified in the tobacco-pith tissue cultures. It was not a substrate for adenosine deaminase and not incorporated into tRNA. The relative biological activities in the tobacco-tissue culture bioassay suggested that the modification of the ribosyl moiety of N6-(Δ2-isopentenyl) adenosine reduced but did not abolish its ability to promote cell growth.