(1-Benzimidazolonyl)alanine (Bia): preliminary investigations into a potential tryptophan mimetic

The new amino acid (1-benzimidazolonyl)alanine (Bia) was synthesized as a potential biomimetic replacement of tryptophan. The replacement of tryptophan with this amino acid in a truncated analog of p53 showed nearly identical binding to HDM2 as the same length of the natural peptide. Similar peptides containing 1- and 2-naphthylalanine in lieu of Trp showed weaker binding than either of the other peptides. The synthesis of Bia and the binding of the p53 analogs to HDM2 are reported.