O

[101

Figure 5 Bioallethrin structures.

NH-Protein

[101

Figure 5 Bioallethrin structures.

and conjugation to protein led to an immunogen (Fig. 5 [11]) by means of which stereoselective antibodies were obtained. A lzsI-Iabeled tyramine conjugate (Fig. 5 [10]) was used as the radioligand. All eight isomers were studied for their ability to inhibit radioligand binding. As Table 1 shows, the enantiomer [9b] of compound [9a] (Fig. 5) had less than 1% cross-reaction. Changing only the asymmetric center at the 4' position is less critical for binding than changing the orientation of the groups on the

Table 1 Stereochemistry and Antibody Binding in the Bioallethrin Series3

Cyclopropane substituent Compound orientation

Absolute configuration

— Percent cross-reaction 4' at 50% inhibition

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