A series of receptors were prepared all containing two adenine binding
sites linked by various spacers. Their ability to act as templates in
the coupling of two adenine derivatives, an active ester and an amine
, in CHCl3 was evaluated. The accelerations varied from none to 700-fo
ld. Binding studies of the coupling product with these templates confi
rmed involvement of both binding sites. When the spacer was a 1,10-phe
nanthroline unit, an efficient hydrolysis reaction of the active ester
was observed. Another series of receptors were prepared containing on
e adenine receptor and various polar functional groups. The molecules
were evaluated as catalysts in the coupling of an adenine-derived acti
ve eater and n-butylamine. The orientation as well as the nature of th
e functional group greatly influenced the coupling rate. A carboxylate
group was most effective, accelerating the intracomplex reaction 250-
fold.