252664-13-4

Upstream product

• 67462-20-8 (1R,2S)-N-amino-2-methylamino-1-phenyl-1-propanol 
• 38256-17-6 3-(5-formyl-4-methoxycarbonylmethyl-pyrrol-3-yl)-propionic acid methyl ester 
• 50-98-6 ephedrine hydrochloride 
• 1850-61-9 (1R,2S)-N-methyl-N-nitroso-2-amino-1-phenyl-1-propanol 

Downstream Products

• 252664-34-9 C₂₂H₂₈⁽²⁾HN₃O₅ 

Relevant academic research and scientific papers

Synthesis of (11S)- and (11R)-Porphobilinogen; Stereochemical Studies on Hydroxymethylbilane Synthase (PBG Deaminase)

(11S)- and (11R)-Porphobilinogen (PBG) are synthesized and their configurations are estabilished by degradation to a derivative of (2)H1-glycine; they are used to prove that when hydroxymethylbilane synthase (PBG deaminase) acts on PBG in the pr

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)

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.