P. Schwinte et al., DITOPIC BINDING OF NUCLEOTIDES BY KIS(6-HYDROXYETHYLAMINO-6-DEOXY)-BETA-CYCLODEXTRIN, Perkin transactions. 2, (4), 1998, pp. 805-808
The potential of heptakis(6-hydroxyethylamino-6-deoxy)-beta-(1) as a d
itopic receptor capable of electrostatic interaction and hydrogen bond
ing by its amino side-chains, together with inclusion in its hydrophob
ic cavity, has been assessed for nucleotides as guest molecules. The i
nteraction of 1 with adenosine-5'-triphosphate (ATP) and adenosine-5'-
monophosphate (AMP) has been studied by potentiometry in water. Except
ionally strong binding is observed for fully protonated 1 with ATP(4-)
(K = 10(10) M-1) relative to AMP(2-) (K = 10(6) M-1), consistent with
stronger electrostatic interaction with the former. Binding of AMP an
d p-nitrophenyl phosphate is of the same order of magnitude, while the
complexes formed with ribose-5-phosphate are much weaker, The NMR cha
nges observed upon addition of the nucleotides to 1 confirm interactio
n with the amino sites, together with inclusion in the cyclodextrin ca
vity.