A convenient catalytic silicon-assisted route towards new non-proteinogenic amino acids with methylenebisphosphonic acids moieties

Abstract

The new non-proteinogenic amino acids with methylenebisphosphonic acids moieties are synthesized for the first time via unique reaction of tris(trimethylsilyl) phosphite and various N-formyl amino acids at the presence of effective catalyst – trimethylsilyl triflate under mild conditions. The further treatment of initially formed trimethylsilyl intermediates with the methanol excess resulted in the water-soluble non-proteinogenic amino acids with methylenebisphosphonic acids moieties in high yields. The catalytic scheme of target substances formation is proposed and discussed in detail. The structures of target functionalized amino acids and their precursors were confirmed by the 1H, 13C, 31P NMR spectra and high resolution mass spectra. The resulted compounds are of great interest as promising antiviral substances and effective ligands.