Kasser Johanna, Nazarov Alexey A, Hartinger Christian G, Wdziekonski Brigitte, Dani Christian, Kuznetsov Maxim L, Arion Vladimir B, Keppler Bernhard K
University of Vienna, Institute of Inorganic Chemistry, Vienna, Austria.
Bioorg Med Chem. 2009 May 1;17(9):3388-93. doi: 10.1016/j.bmc.2009.03.039. Epub 2009 Mar 26.
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 C(alpha)-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.
