BISUBSTRATE REACTION TEMPLATES - EXAMINATION OF THE CONSEQUENCES OF IDENTICAL VERSUS DIFFERENT BINDING-SITES

A reaction template (1≈9) possessing two binding sites is described. The template was designed to use hydrogen bonding to simultaneously (but transiently) bind two substrates, giving rise to a ternary complex (2≈12), which positions the substrates in an orientation that facilitates reaction between them. Bisubstrate reaction template 9 was synthesized and shown to accelerate the reaction between substrates 10 and 11. Control studies support the proposed intermediacy of ternary complex 12. A second template (41), where-in contrast to 9-the two binding sites are different, is also described. In accordance with prediction, 41 is more effective than 9 at promoting the reaction of its substrates. The reaction promoted by 41 was also shown to be subject to competitive inhibition. © 1990, American Chemical Society. All rights reserved.