New Phosphorus Chemistry Leads to Unnatural Aminoacid Trimers

Unnatural or modified amino acids have become important biochemical vectors because of their potential utility in diagnostic or therapeutic medicine. Our ongoing research in hydroxymethyl phosphine chemistry has provided unique reaction pathways to produce unnatural aminoacid. The reaction of tris(hydroxymethyl)phosphine (THP) with chiral aminoacid L-alanine produced trimeric alanine in excellent yields. The X-ray crystal structure of 1 shows an unusual layered structure with water molecules sandwiched between the layers. Implications of this new chemistry in such emerging areas as chiral technology and drug discovery will be presented.