Stereospecificity of isotopic exchange of C-α-protons of glycine catalyzed by three PLP-dependent lyases: the unusual case of tyrosine phenol-lyase.

A comparative study of the kinetics and stereospecificity of isotopic exchange of the pro-2R- and pro-2S protons of glycine in (2)H(2)O under the action of tyrosine phenol-lyase (TPL), tryptophan indole-lyase (TIL) and methionine γ-lyase (MGL) was undertaken. The kinetics of exchange was monitored using both (1)H- and (13)C-NMR. In the three compared lyases the stereospecificities of the main reactions with natural substrates dictate orthogonal orientation of the pro-2R proton of glycine with respect to the cofactor pyridoxal 5'-phosphate (PLP) plane.

A novel and efficient method to prepare 2-aryltetrahydrofuran-2-ylphosphonic acids.

A novel one-pot method was developed for the synthesis of the title compounds starting from 4-chloro-1-aryl-1-butanones 1, phosphorus trichloride and acetic acid. The end products 2 were obtained in 20-94% yield. The cyclization step under acidic conditions probably occurs as a result of anchimeric assistance of the phosphonic acid group.