A one step/one pot synthesis of N,N-bis(phosphonomethyl)amino acids and their effects on adipogenic and osteogenic differentiation of human mesenchymal stem cells

The one pot reaction of amino acids with diethylphosphite and formaldehyde yielded N,N-bis(phosphonomethyl)amino acids. This synthetic route does not require harsh reagents to cleave the ester group. The molecular structures of the new compounds were determined by X-ray diffraction methods. By employing DFT calculations the hydrolysis of the intermediate phosphonic esters to the respective acids could be explained by the decreasing P–OEt bond strength for Cα-bisalkylated amino acids. Biological evaluation on the adipogenic and osteogenic differentiation of mesenchymal stem cells revealed no modification of the adipocyte differentiation, but inhibition of osteoblast formation at concentrations without detectable cytotoxicity.

N,N-Bis(phosphonomethyl)amino acids were synthesized in a one step-one pot procedure. Biological studies on the effects on the adipogenic and the osteogenic differentiation of mesenchymal stem cells were performed.Figure optionsDownload as PowerPoint slide