Biosynthesis of porphyrins and related macrocycles. Part 53. Stereochemical studies on the enzymic formation of hydroxymethylbilane, the precursor of …

JR Schauder, S Jendrezejewski, WL Neidhart…

Index: Schauder, Jean-Roch; Jendrezejewski, Stefan; Neidhart, Werner L.; Hart, Graham J.; Battersby, Alan R. Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 19 p. 2691 - 2698

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Abstract

A new synthesis of porphobilinogen 1 (PBG) is described that allows the preparation of (11R)-[11-3H1] PBG 1a and its (11S)-enantiomer 1b. Their enantiomeric purities are determined by degradation of their immediate synthetic precursors by way of 3H-labelled glycines to yield two samples of 3H-labelled glycolic acid 16. The enzyme glycolate oxidase, known to remove HR stereospecifically from the methylene group of glycolic acid in ...

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