Pairs of probes with recognition elements of opposite configuration can be used to detect target proteins of biologically active natural products. The diastereomeric probes shown were designed on the basis of structure–activity relationships determined for an endogenous factor that controls leaf opening and closing in the title plant. They revealed that a 38 kDa membrane protein is key to the stereospecific recognition of the natural product.

Albizzia saman, a leguminous plant, is known to open its leaves in the daytime and sleep at night with the leaves folded. -D-Glucopyranosyl 12-hydroxyjasmonate (1) was isolated as an endogenous chemical factor controlling this leafmovement. We developed a concise synthesis of optically pure (À)-1 in 9 steps from (+)-2 with a total yield of 58%. Similarly, such analogs of 1 as epi-LCF (13), enantiomer (14), and galactoside (19) were synthesized for a structure activity relationship (SAR) study. The results of this SAR study strongly suggest that the mechanism for the leaf-closing activity of 1 would be different from that of methyl jasmonate, and also suggest the involvement of a different kind of target protein which recognizes the trans-isomer of a jasmonate derivative.

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