Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 2, Pages 764-767Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo702319n
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[GRAPHICS] A practical synthesis of porphobilinogen based on the biosynthetic mechanism is described. The crossed Mukayiama. aldol reaction is the key step creating the central carbon-carbon bond between the two protected forms of 5-aminolevulinic acids. The optimized sequence gives a crystalline, storable precursor, which can be transformed in high yield into porphobilinogen and bioconjugates thereof. The enzymatic hydrolysis of the precursor produces porphobilinogen in quantitative yield.
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