Synthesis of (11S)- and (11R)-[11-2H1]porphobilinogen; stereochemical studies on hydroxymethylbilane synthase (PBG deaminase)
Abstract
(11S)-and (11R)-[11-2H1]Porphobilinogen (PBG) are synthesized and their configurations are established by degradation to a derivative of 2H1-glycine; they are used to prove that when hydroxymethylbilane synthase (PBG deaminase) acts on PBG in the presence of ammonia, aminomethylbilane is formed with overall retention of configuration at the NH2CHD-group.