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American Chemical Society, Journal of Organic Chemistry, 2(73), p. 764-767, 2007

DOI: 10.1021/jo702319n

Wiley-VCH Verlag, ChemInform, 21(39), 2008

DOI: 10.1002/chin.200821113

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Facile Synthesis of a “Ready to Use” Precursor of Porphobilinogen and Its Amino Acid Derivatives

This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

(Chemical Equation Presented) 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.