Binaphthyl derivatives as ditopic receptors for amino acids

ORGN 18

Vladimir Sidorov, vasidorov@vcu.edu and Ibrahim Hamdi Zgani. Department of Chemistry, Virginia Commonwealth University, 1001 West Main Street, Richmond VA, VA 23284
Amino acids exist as strongly solvated zwitterions in neutral solutions and their extraction and transport through the lipophilic membranes is very difficult. Thus, synthetic amino acids receptors has attracted great interest in supramolecular chemistry due to the immense biological significance and practical importance of these molecules. In this work, we describe the synthesis of new amino acids receptors comprising a binaphthyl core bearing two 15-aza-crown-5 groups on one side and self-complementary arms bearing amino acid-binding moieties (R1 and R2) on the other side. In the compound (1), (R1=R2) is a α-aminophosphonate chain and in compound 2 R1 is an aliphatic chain bearing an ammo group and R2 comprises a carboxylic moiety. The effect of sodium or potassium salts on the affinity of these compounds toward different amino acids has been discussed and their ability to transport amino acids across liquid membranes evaluated.