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Figure 1.
Fig. 1. Reaction scheme and haptens used in this study.
The retro-Diels-Alder reaction of pro-drug 1a (k[un] = 9.8 10^
 6 s
1
conditions: 31°C in PBS pH 7.4, 10% vol/vol
dimethylformamide) releases nitroxyl and anthracene 2a. The
reaction is catalyzed by antibodies 9D9 (anti-3), 10F11
(anti-5), and 27C5 (anti-3,4). The reaction with the
regioisomeric substrate 1b (k[un] = 7.1 10^ 6 s
1) is
also catalyzed weakly by the antibodies. The unreactive
substrate analog 6 and product analogue 2b were used for
crystallization. Substrate analogue 1c and product analog 2c and
transition state model 7 were used for docking studies.
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