Facile synthesis of a "ready to use" precursor of porphobilinogen and its amino Acid derivatives.
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.
Soldermann
Carole Pissot
CP
Institut de Chimie, Université de Neuchatel, Rue Emile-Argand 11, PO 158, CH-2009 Neuchatel, Switzerland.
Vallinayagam
Ramakrishnan
R
Tzouros
Manuel
M
Neier
Reinhard
R
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011162:Porphobilinogen / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D011162:Porphobilinogen