29261-13-0Relevant articles and documents
Biosynthesis of porphyrins and related macrocycles. Part 52.1'2 Synthesis of 1-SH11-4Hjporphobilinogen and the (11R)enantiomer for stereochemical studies on hydroxymethylbilane synthase (porphobilinogen deaminase)
Neidhart, Werner L.,Anderson, Paul C.,Hart, Graham J.,Battersby, Alan R.
, p. 2677 - 2689 (2007/10/03)
A synthetic route is devised for the synthesis of (115)-[11-2H,]porphobilinogen la and of the (1 lβ)-enantiomer Ib. Their absolute configurations and enantiomeric purity are established by degradation to a derivative of [2-2H,]glycine of known stereochemistry. Methods are then developed, based on the synthesis of chiral imidate esters, for determination of the configuration of [2H1]-labelled aminomethylpyrroles by converting them into [2H,]-labelled amidines followed by analysis using 'H-NMR. The labelled samples of PEG la and Ib serve as substrates for hydroxymethylbilane synthase and the products are trapped as [2H1]-labelIed aminomethylbilanes 7c and 7d. Their configurations are determined by the NMR assay to demonstrate that as PBG 1 is enzymically converted into the aminomethylbilane 7, there is overall retention of configuration at the aminomethyl carbon. The Royal Society of Chemistry 1999.
