Synthesis of (2R)- and (2S)-[1-13C]-2-amino-2-methylmalonic acid, probes for the serine hydroxymethyltransferase reaction: stereospecific decarboxylation of the 2-pro-R carboxy group with the retention of configuration

Abstract

2-Amino-2-methylmalonic acid and both of its [1-¹³C]-enantiomers were synthesised and were then used to probe the stereochemical course and mechanism of serine hydroxymethyltransferase catalysed reactions; the pro-R carboxy group of 2-amino-2-methylmalonic acid was decarboxylated and was replaced by a proton with retention of configuration at C-2 to give (2R)-alanine.