110728-00-2Relevant academic research and scientific papers
One-pot, regioselective synthesis of substituted arylglycines for kinetic resolution by penicillin G acylase
Grundmann, Peter,Fessner, Wolf-Dieter
experimental part, p. 1729 - 1735 (2009/07/24)
Amido-alkylation of electron-rich arenes with phenylacetamide and glyoxylic acid offers an in-expensive route to a large variety of N-phenylacetylated arylglycines that are suited for immediate enzymatic resolution by penicillin G acylase. When performed under mild conditions at 5 °C in acetic acid/HCl, this simple one-pot operation resulted in the formation of single regioisomers only (≥98%). Subsequent kinetic resolution of the amino acid derivatives by penicillin G acylase at pH 8.0 occurred generally with E values >100 and thus furnished free (S)-configurated arylglycines with high enantiomeric purity. The corresponding enantiopure (R)-substrates, easily separable by a phase-selective extraction process, provided the corresponding (R)-enantiomers upon conventional hydrolysis. This one-pot, two-step procedure for arylglycine synthesis, resolution and work-up requires a minimum of equipment and grants rapid access to both enantiopure (S)- and (R)-antipodes of non-natural α-amino acids in small-to large-scale quantities.
