Facile Synthesis of a "Ready to Use" Precursor of Porphobilinogen and Its Amino Acid Derivatives
Author(s)
Soldermann-Pissot, Carole
Vallinayagam, Ramakrishnan
Tzouros, Manuel
Date issued
2008
In
J. Org. Chem.
Vol
2
No
73
From page
764
To page
767
Subjects
Amino acids Role: SPN (Synthetic preparation) PREP (Preparation) (conjugates prepn. of a precursor of porphobilinogen and its amino acid conjugates) Aldol condensation (crossed Mukayiama aldol reaction between silyl enol ethers and acyl cyanides) amino acid porphobilinogen precursor prepn crossed Mukayiama aldol reaction
Abstract
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 cryst., storable precursor, which can be transformed in high yield into porphobilinogen and bioconjugates thereof. The enzymic hydrolysis of the precursor produces porphobilinogen in quant. yield. [on SciFinder(R)]
Publication type
journal article